Lubricant Compositions Comprising Epoxide Compounds

ABSTRACT

A lubricant composition including an epoxide compound is disclosed. An additive package including the epoxide compound is also disclosed. The epoxide compound of the lubricant composition acts to improve compatibility of the lubricant composition with a fluoropolymer seal and improve the total base number of the lubricant composition.

RELATED APPLICATIONS

This application claims priority to U.S. Provisional Patent ApplicationNo. 61/727,414, filed on Nov. 16, 2012, which is incorporated byreference herein in its entirety.

FIELD OF THE INVENTION

The present invention generally relates to a lubricant composition thatincludes a base oil and an epoxide compound. The invention also relatesto an additive package for a lubricant composition and to a method oflubricating a system including a fluoropolymer seal.

BACKGROUND OF THE INVENTION

It is known and customary to add stabilizers to lubricant compositionsbased on mineral or synthetic oils in order to improve their performancecharacteristics. Some conventional amine compounds are effectivestabilizers for lubricant compositions. These conventional aminecompounds may help neutralize acids formed during the combustion processwhen the lubricant compositions are utilized in combustion engines.However, these conventional amine compounds are generally not employedin combustion engines due to their detrimental effects on fluoropolymerseals.

It is an object of the present invention to provide new types oflubricant compositions having improved fluoropolymer seal compatibilityand improved neutralization.

SUMMARY OF THE INVENTION

The present invention provides a lubricant composition. The lubricantcomposition includes a base oil and an additive package. The additivepackage includes an epoxide compound having two or more oxirane rings,wherein at least one of the oxirane rings is terminal. The additivepackage also includes an antiwear additive that contains phosphorous.The additive package is present in an amount of at least 5 wt. % basedon a total weight of the lubricant composition.

Alternatively, the present invention provides a lubricant compositionthat includes an additive package which includes an epoxide compoundhaving two or more oxirane rings and having an epoxide equivalent weightof from 75 to 250 g per mole of oxirane ring in the epoxide compound;and the antiwear additive includes phosphorous.

Furthermore, the present invention provides a lubricant composition thatincludes a base oil; an epoxide compound having two or more oxiranerings, wherein at least one of the oxirane rings is terminal; and anantiwear additive includes phosphorous. The lubricant composition has atotal additive treat rate of at least 5 wt. % based on a total weight ofthe lubricant composition.

The present invention is also directed to a method of lubricating asystem that includes a fluoropolymer seal. The method includes providinga lubricant composition that includes a base oil and an additivepackage. The additive package includes an epoxide compound including twoor more oxirane rings, wherein at least one of the oxirane rings isterminal, and an antiwear additive that contains phosphorous. The methodalso includes contacting the fluoropolymer seal with the lubricantcomposition. The additive package is present in an amount of at least 5wt. % based on a total weight of the lubricant composition.

Further still, the present invention provides an additive package for alubricant composition. The additive package includes an epoxide compoundhaving two or more oxirane rings, wherein at least one of the oxiranerings is terminal. The additive package also includes an antiwearadditive that contains phosphorous.

Lubricant compositions including the epoxide compound demonstrateimproved compatibility with fluoropolymer seals as demonstrated by CECL-39-T96 and improved neutralization ability as demonstrated by ASTMD4739 and ASTM D2896.

DETAILED DESCRIPTION

The lubricant composition or additive package includes at least oneepoxide compound. In some embodiments, the epoxide compound may berepresented by general formula (I):

In general formula (I), each R is independently a hydrogen atom or ahydrocarbyl group. Multiple groups designated by R may be bondedtogether to form a cyclic structure.

The term “cyclic” is intended to refer to compounds that include anymolecules having at least three atoms joined together to form a ring. Insome embodiments, the term “cyclic” does not include aromatic compounds.

The epoxide compound may include one or more oxirane ring. The oxiranering may be a terminal oxirane ring or an internal oxirane ring. Theterm “terminal oxirane ring” means that one of the carbon atoms whichform the oxirane ring must contain two hydrogen atoms, or that twocarbons which form the oxirane ring also form part of a cyclic ring. Theterm “internal oxirane ring” means that neither of the carbon atomswhich form the oxirane ring is bonded to more than one hydrogen atom.The epoxide compound may be free from internal oxirane rings, or mayinclude fewer than 4, 3, 2, or 1, internal oxirane rings. Alternatively,the epoxide compound may include 1, 2, 3, 4, or more internal oxiranerings. Alternatively still, the epoxide compound may include at least 1,at least 2, at least 3, at least 4 terminal oxirane rings. In certainembodiments, at least one, or at least two, oxirane rings may beterminal and may be cyclic, i.e, the carbons of the oxirane rings arepart of a cyclic ring.

Each hydrocarbyl group designated by R may independently be substitutedor unsubstituted, straight or branched, alkyl, alkenyl, cycloalkyl,cycloalkenyl, aryl, alkylaryl, arylalkyl group, or combinations thereof.Each hydrocarbyl group designated by R may independently include from 1to 100, 1 to 50, 1 to 40, 1 to 30, 1 to 20, 1 to 15, 1 to 10, 1 to 6, or1 to 4, carbon atoms. Alternatively, each hydrocarbyl group designatedby R may independently include less than 20, less than 15, less than 12,or less than 10, carbon atoms.

By “unsubstituted,” it is intended that the designated hydrocarbyl groupor hydrocarbon group is free from substituent functional groups, such asalkoxy, amide, amine, keto, hydroxyl, carboxyl, oxide, thio, and/orthiol groups, and that the designated hydrocarbyl group or hydrocarbongroup is free from heteroatoms and/or heterogroups.

Alternatively, each hydrocarbyl group designated by R may beindependently substituted, and include one or more heteroatoms, such asoxygen, nitrogen, sulfur, chlorine, fluorine, bromine, or iodine, and/orone or more heterogroups, such as pyridyl, furyl, thienyl, andimidazolyl. Alternatively, or in addition to including heteroatoms andheterogroups, each hydrocarbyl group designated by R may independentlyinclude one or more substituent groups selected from alkoxy, amide,amine, carboxyl, epoxy, ester, ether, hydroxyl, keto, metal salt,sulfuryl, and thiol groups. Alternatively, each hydrocarbyl groupdesignated by R may be independently unsubstituted.

Exemplary alkyl groups include methyl, ethyl, propyl, isopropyl,n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, iso-amyl, hexyl,2-ethylhexyl, octyl and dodecyl groups. Exemplary cycloalkyl groupscyclopropyl, cyclopentyl and cyclohexyl groups. Exemplary aryl groupsinclude phenyl and naphthalenyl groups. Exemplary arylalkyl groupsinclude benzyl, phenylethyl, and (2-naphthyl)-methyl.

As described above with respect to general formula (I), the hydrocarbylgroup designated by R may include one or more epoxy groups. Thesehydrocarbyl epoxy groups may be represented by the general formula (II):

In general formula (II), R¹ is a divalent hydrocarbon group and each R²may independently be a hydrogen atom or a hydrocarbyl group. Thedivalent hydrocarbon group designated by R¹ may be substituted orunsubstituted, straight or branched, alkyl, alkenyl, cycloalkyl,cycloalkenyl, aryl, alkylaryl, arylalkyl group, or combinations thereof.Each hydrocarbon group designated by R¹ may independently include from 1to 100, 1 to 50, 1 to 40, 1 to 30, 1 to 20, 1 to 15, 1 to 10, 1 to 6, or1 to 4, carbon atoms. Alternatively still, each hydrocarbyl groupdesignated by R¹ may independently include less than 20, less than 15,less than 12, or less than 10, carbon atoms. Alternatively, eachhydrocarbon group designated by R¹ may be independently substituted, andinclude one or more heteroatoms, such as oxygen, nitrogen, sulfur,chlorine, fluorine, bromine, or iodine, and/or one or more heterogroups,such as pyridyl, furyl, thienyl, and imidazolyl. Alternatively, or inaddition to including heteroatoms and heterogroups, each hydrocarbongroup designated by R¹ may independently include one or more substituentgroups selected from alkoxy, amide, amine, carboxyl, epoxy, ester,ether, hydroxyl, keto, metal salt, sulfuryl, and thiol groups. Thehydrocarbyl groups designated by R² may have the same meaning as R asdescribed above with respect to general formula (I). Multiple groupsdesignated by R² may be bonded together to form a cyclic structure.

Referring again to general formula (I), if at least one R is ahydrocarbyl group including an amide group, exemplary epoxide compoundsinclude N-methyl 2,3-epoxypropionamide, N-ethyl 2,3-epoxypropionamide,N-propyl 2,3-epoxypropionamide, N-isopropyl 2,3-epoxypropionamide,N-butyl 2,3-epoxypropionamide, N-isobutyl 2,3-epoxypropionamide,N-tert-butyl 2,3-epoxypropionamide, N-hexyl 2,3-epoxypropionamide,N-octyl 2,3-epoxypropionamide, N-(2-ethylhexyl)-2,3-epoxypropionamide,and N-dodecyl 2,3-epoxypropanionamide.

In certain embodiments, the epoxide compound of general formula (I) maybe an alkyl epoxide compound. The alkyl epoxide compound may beexemplified by 1,2-epoxybutane, 2-methyl 2,3-epoxy butane,1,2-epoxypentane, 1,2-epoxyhexane, 1,2-epoxyheptane, 1,2-epoxyoctane,1,2-epoxynonane, 1,2-epoxydecane, 1,2-epoxyundecane, 1,2-epoxydodecane,1,2-epoxytridecane, 1,2-epoxytetradecane, 1,2-epoxypentadecane,1,2-epoxyhexadecane, 1,2-epoxyheptadecane, 1,1-,2-epoxyoctadecane,1,2-epoxynonadecane, and 2,3-epoxy pentane.

Alternatively, in other embodiments, the epoxide compound of generalformula (I) may be an alkyl glycidyl ether compound. The alkyl glycidylether compound may be exemplified by decyl glycidyl ether, undecylglycidyl ether, dodecyl glycidyl ether, tridecyl glycidyl ether,tetradecyl glycidyl ether, 2-ethylhexyl glycidyl ether, neopentyl glycoldiglycidyl ether, trimethylolpropane triglycidyl ether, pentaerythritoltetraglycidyl ether, 1,6-hexane diol diglycidyl ether, sorbitolpolyglycidyl ether, polyalkylene glycol monoglycidyl ether, andpolyalkylene glycol diglycidyl ether.

Exemplary epoxide compounds also include glycidol, glycidol derivatives,glycidyl, glycidyl derivatives, allyl 2,3-epoxypropyl ether, isopropyl2,3-epoxypropyl ether, (tert-butoxymethyl)oxirane, and[[(2-ethylhexyl)oxy]methyl]oxirane.

In some embodiments, the epoxide compound may be an epoxide estercompound. The epoxide ester compound may be represented by generalformula (III):

In general formula (III), each group designated by R³ is independently ahydrogen atom or a hydrocarbyl group, and wherein at least one groupdesignated by R³ is an epoxy group or is a hydrocarbyl group substitutedwith an epoxy group. Alternatively, in certain embodiments, each groupdesignated by R³ is an epoxy group or a hydrocarbyl group substitutedwith at least one epoxy group. Further still, at least one of the groupsdesignated by R³ in general formula (III) may designate a cyclichydrocarbyl group where two carbons of the oxirane ring are part of thecyclic ring. The hydrocarbyl groups designated by R³ may independentlyhave the same meaning as R described above with respect to generalformula (I).

The epoxide ester compound of general formula (III) may be exemplifiedby methyl 2,3-epoxypropionate, ethyl 2,3-epoxypropionate, propyl2,3-epoxypropionate, isopropyl 2,3-epoxypropionate, butyl2,3-epoxypropionate, isobutyl 2,3-epoxypropionate, hexyl2,3-epoxypropionate, octyl 2,3-epoxypropionate, 2-ethylhexyl2,3-epoxypropionate, and dodecyl 2,3-epoxypropionoate.

In certain embodiments, the epoxide ester compound of general formula(III) may be more specifically represented by general formula (IV):

In general formula (IV), each group designated by R⁴ may be a hydrogenatom or a hydrocarbyl group. The hydrocarbyl group designated by R⁴ mayhave the same meaning as R described above with respect to generalformula (I). The epoxide ester compound of general formula (IV) may beexemplified by glycidyl-2,2-dimethyl octanoate, glycidyl benzoate,glycidyl-tert-butyl benzoate, glycidyl acrylate, and glycidylmethacrylate.

In certain embodiments, the epoxide compound is a cyclic epoxidecompound. The cyclic epoxide compound may be represented by generalformula (V):

In general formula (V), Z represents the type and number of atomsnecessary to complete the cyclic ring of general formula (V). The ringdesignated by Z may include from 2 to 20, 3 to 15, 5 to 15, carbonatoms. For example, the ring designated by Z may include 1, 2, 3, 4, 5,6, 7, 8, 9, 10, 11, or 12 carbons, not accounting for the number ofcarbon atoms in any substituent groups. Z may be a substituted orunsubstituted, branched or unbranched, divalent hydrocarbon group thatmay include one or more heteroatoms, such as oxygen, nitrogen, sulfur,chlorine, fluorine, bromine, or iodine, or one or more heterogroups,such as pyridyl, furyl, thienyl, and imidazolyl. In addition to, oralternatively to, including heteroatoms and/or heterogroups, the ringdesignated by Z may include one or more hydrocarbyl substituent groups,such as those described for R¹ in general formula (I). The divalenthydrocarbon group designated by Z may be aliphatic or aromatic. In someembodiments, the divalent hydrocarbon group designated by Z may beexemplified by: cyclopropyl, cyclopentyl, cyclohexyl, phenyl,naphthalenyl, benzyl, phenylethyl, and (2-naphthyl)-methyl groups. Itshould be appreciated that the heteroatoms, heterogroups, and/orsubstituent groups described above may be bonded to various atoms in thering designated by Z; for example, the hydrocarbyl substituent groupsmay be bonded directly to one or more carbons in the ring designated byZ that form part of the oxirane ring. Alternatively, the substituentgroups, heterogroups, and heteroatoms may be bonded to other carbonatoms in the hydrocarbon group, such as carbons that are not part of theoxirane ring. In some embodiments, the cyclic epoxide compound ofgeneral formula (V) may be a cycloaliphatic epoxide compound having atleast two terminal oxirane rings.

The cyclic epoxide compound of general formula (V) may be exemplified by1,2-epoxycyclohexane, 1,2-epoxycyclopentane,3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexane carboxylate,bis(3,4-epoxy cyclohexylmethyl) adipate,bis(3,4-epoxy-6-methylcyclohexylmethyl) adipate, and4-epoxyethyl-1,2-epoxycyclohexane.

As should be appreciated from general formulas (I), (II), (III), (IV),and (V) described above, the epoxide compound may be a monoepoxide, or apolyepoxide compound, such as a diepoxide. The polyepoxide compoundincludes at least two oxirane rings. Furthermore, in some embodiments,the polyepoxide compound may include fewer than 10, fewer than 8, fewerthan 5, fewer than 4, or fewer than 3, oxirane rings per molecule.

The polyepoxide compound may include one or more substituted orunsubstituted, branched or unbranched, hydrocarbyl or divalenthydrocarbon groups, such alkyl, alkenyl, cycloalkyl, alkylcycloalkyl,aryl, alkylaryl group, arylalkyl groups, and combinations thereof. Eachhydrocarbyl or divalent hydrocarbon group included in the polyepoxidecompound may independently be substituted with one or more heteroatoms,such as oxygen, nitrogen, sulfur, chlorine, bromine, fluorine, oriodine, and/or may independently include one or more heterogroups, suchas pyridyl, furyl, thienyl, and imidazolyl. Each hydrocarbyl or divalenthydrocarbon group in the polyepoxide compound may include one or moresubstituent groups selected from alkoxy, amide, amine, carboxyl, epoxy,ester, ether, hydroxyl, keto, metal salt, sulfuryl, and thiol groups.Each of the hydrocarbyl or divalent hydrocarbon groups in thepolyepoxide compound may independently include from 1 to 100, 1 to 50, 1to 40, 1 to 30, 1 to 20, 1 to 10, 1 to 6, or 1 to 4, carbon atoms. Thehydrocarbyl or divalent hydrocarbon groups may be bonded to one anotheror to one or more carbon atoms of the oxirane rings to form thepolyepoxide compound.

In some embodiments, the polyepoxide compound may be represented by thegeneral formula (VI):

In general formula (VI), R⁵, R⁶, R⁷, R⁸ and R⁹ are each independently ahydrogen atom or a hydrocarbyl group. R¹⁰ is a divalent hydrocarbongroup. The hydrocarbyl groups designated by R⁵, R⁶, R⁷, R⁸, and R⁹ ingeneral formula (VI) may have the same meaning as described above withrespect to R in general formula (I). The divalent hydrocarbon groupdesignated by R¹⁰ in general formula (VI) may have the same meaning asdescribed above with respect to R¹ in general formula (II). In certainembodiments, R⁵ and R⁶, together with the two carbons of the oxiranering, form a cyclic structure. In other embodiments, R⁷ and R⁸, togetherwith the two carbons of the oxirane ring, form a cyclic structure. Assuch, the polyepoxide compound of general formula (VI) may include one,two, or more than two, cyclic rings. Furthermore, in certainembodiments, at least one, or at least two, of the oxirane oxygens ingeneral formula (VI) is directly bonded to two cyclic carbons, i.e.,carbons which form part of a cyclic ring.

Alternatively, the polyepoxide compound may be represented by generalformula (VII) shown below:

In general formula (VII), each Z may have the same meaning as describedabove with respect to general formula (V). In general formula (VII), R¹¹is a divalent hydrocarbon group. R¹¹ may have the same meaning asdescribed above with respect to R¹ in general formula (II). It should beappreciated that the divalent hydrocarbon group designated by R¹¹ may bebonded to various atoms in the divalent hydrocarbon group designated byZ. For example, the divalent hydrocarbon group designated by R¹¹ may bebonded directly to one or more oxirane ring carbons in certainembodiments. Alternatively, the divalent hydrocarbon group designated byR¹¹ may be bonded to non-oxirane ring carbon atoms in the hydrocarbongroup designated by Z. The polyepoxide compound of general formula (VII)may be exemplified by:

-   3-(1-(6-oxabicyclo[3.1.0]hexan-3-yl)propyl)-7-oxabicyclo[4.1.0]heptane:

-   3-((7-oxabicyclo[4.1.0]heptan-3-yl)methyl)-8-oxabicyclo[5.1.0]octane:

-   4-[1-(7-oxabicyclo[4.1.0]heptan-4-yl)propyl]-7-oxabicyclo[4.1.0]heptane:

-   4-[1-methyl-1-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]-7-oxabicyclo[4.1.0]heptane:

In one specific embodiment, the polyepoxide compound may be apolyepoxide ester compound including at least two oxirane rings. Incertain embodiments, the polyepoxide ester compound may be exemplifiedby the general formula (VIII):

In general formula (VIII), each Z may have the same meaning as describedabove with respect to general formula (V). In general formula (VIII),R¹² is a divalent hydrocarbon group. R¹² may have the same meaning asdescribed above with respect to R¹ in general formula (II). It should beappreciated that the divalent hydrocarbon group designated by R¹² may bebonded to various atoms in the divalent hydrocarbon group designated byZ. For example, the divalent hydrocarbon group designated by R¹² may bebonded directly to one or more oxirane ring carbons in certainembodiments. Alternatively, the divalent hydrocarbon group designated byR¹² may be bonded to non-oxirane ring carbon atoms in the ringdesignated by Z. In one embodiment, the epoxide compound of generalformula (VIII) is a 3,4-epoxycycloalkyl, 3,4-epoxy-cycloalkylcarboxylate, such as 3,4-epoxycyclohexylmethyl, 3,4-epoxy-cyclohexanecarboxylate. The polyepoxide ester compound of general formula (VIII)may be exemplified by:

-   3-((7-oxabicyclo[4.1.0]heptane-3-carbonyl)oxy)propyl    9-oxabicyclo[6.1.0]nonane-4-carboxylate:

-   7-((6-oxabicyclo[3.1.0]hexan-2-yl)methoxy)heptyl    7-oxabicyclo[4.1.0]heptane-3-carboxylate:

-   3-((7-oxabicyclo[4.1.0]heptane-3-carbonyl)oxy)-2-(methoxymethyl)-2-methylpropyl    7-oxabicyclo[4.1.0]heptane-2-carboxylate:

-   3-(7-oxabicyclo[4.1.0]heptane-4-carbonyloxy)propyl    7-oxabicyclo[4.1.0]heptane-4-carboxylate:

-   7-(7-oxabicyclo[4.1.0]heptan-4-ylmethoxy)heptyl    7-oxabicyclo[4.1.0]heptane-4-carboxylate:

-   [2-(methoxymethyl)-2-methyl-3-(7-oxabicyclo[4.1.0]heptane-4-carbonyloxy)propyl]7-oxabicyclo[4.1.0]heptane-4-carboxylate:

Alternatively still, the epoxide compound may be exemplified by generalformula (IX):

[A]_(w)[B]_(x)  (IX)

In general formula (IX), each A is independently a hydrocarbyl group ora divalent hydrocarbon group and each B is an epoxy group. The groupdesignated by A may have the same meaning as described above withrespect to R in general formula (I) or R¹ in general formula (II). “w”is an integer having a value of from 0 to 50, and “x” is an integerhaving a value of from 0 to 10, where w+x≧1, and with the proviso thatif x=0, at least one moiety designated by A is a hydrocarbyl groupincluding an epoxy substituent group. “w” may be an integer having avalue of from 1 to 40, 1 to 30, 1 to 20, 1 to 10, 1 to 8, 1 to 5, or 1to 3, and “x” may be an integer having a value of 10, 9, 8, 7, 6, 5, 4,3, 2, or 1. It should be appreciated that groups A and B in generalformula (IX) may be bonded to one another in any order, with varyingnumber of iterations.

The epoxide compound may be exemplified by the following compounds:

-   2,2′-[ethane-1,2-diylbis(oxymethanediyl)]dioxirane:

-   2,2′-[butane-1,4-diylbis(oxymethanediyl)]dioxirane:

-   2,2′-[ethane-1,2-diylbis(sulfanediylmethanediyl)]dioxirane:

-   bis(oxiran-2-ylmethyl)hexanedioate:

-   bis(oxiran-2-ylmethyl)butanedioate:

-   bis(oxiran-2-ylmethyl)(2E)-but-2-enedioate:

-   2,2′-butane-1,4-diyldioxirane:

-   2,2′-[benzene-1,3-diylbis(oxymethanediyl)]dioxirane:

-   2-({3-(oxiran-2-ylmethoxy)-2-[(oxiran-2-ylmethoxy)methyl]propoxy}methyl)oxirane:

-   3-(oxiran-2-yl)-8-oxabicyclo[5.1.0]octane:

-   8-oxabicyclo[5.1.0]oct-3-ylmethyl    8-oxabicyclo[5.1.0]octane-3-carboxylate:

-   N-methyl 2,3-epoxypropionamide:

-   1,2-epoxybutane:

-   decyl glycidyl ether:

-   trimethylolpropane triglycidyl ether:

-   glycidol:-   [[(2-ethylhexyl)oxy]methyl]oxirane:

-   methyl 2,3-epoxypropionate:

-   glycidyl-2,2-dimethyl octanoate:

-   glycidyl benzoate:

-   glycidyl acrylate:

-   1,2-epoxycyclohexane:

-   bis(3,4-epoxy cyclohexylmethyl)adipate:

-   exo-2,3-epoxynorbornane:

-   4-(1′-methylepoxyethyl)-1,2-epoxy-2-methylcyclohexane:

-   3,4-epoxycyclohexylmethyl, 3,4-epoxy-cyclohexane carboxylate:

It should be appreciated that all of these exemplary compounds fallwithin the scope of one or more of the general formulas (I), (III),(IV), (V), (VI), (VII), (VIII), and (IX) and/or within the scope of thewritten description of the epoxide compound.

In certain embodiments, the epoxide compound may be free from nitrogen,sulfur, phosphorous, chlorine, bromine, and/or iodine atoms. Asdescribed above, the epoxide compound may be aliphatic, cyclic, acyclic,and/or aromatic.

The epoxide compound may have a weight average molecular weight of from44 to 1000, 50 to 750, 100 to 500, 100 to 400, or 100 to 200.Alternatively still, the epoxide compound may have a weight averagemolecular weight of at least 30, at least 50, at least 70, at least 90,at least 110, or at least 130. Alternatively, the epoxide compound mayhave a weight average molecular weight of less than 1500, less than1300, less than 1100, less than 900, less than 700, less than 500, lessthan 400, or less than 300.

The epoxide compound may have an epoxide equivalent weight of from 75 to300, 75 to 250, 75 to 200, 85 to 190, 85 to 175, 95 to 160, or 100 to145, g per mole of oxirane ring of the epoxide compound. Alternatively,the epoxide compound may have an epoxide equivalent weight of at least50, 60, 70, 80, 90, 100, 110, 120, 130, 140, or 150, g per mole ofoxirane ring of the epoxide compound. As referred to throughout thisdisclosure, the term “epoxide equivalent weight” is the numerical valuewhich is obtained by dividing the weight average molecular weight of theepoxide compound by the number of oxirane rings in the molecule.

The basicity effect of the epoxide compound can be determined by acidtitration. The resulting neutralization number is expressed as the totalbase number (TBN), and can be measured using various methods. ASTM D4739is a potentiometric hydrochloric acid titration. The ASTM D4739 methodis favored in engine tests and with used oils to measure TBNdepletion/retention. When testing used engine lubricants, it should berecognized that certain weak bases are the result of the service ratherthan having been built into the oil. This test method can be used toindicate relative changes that occur in lubricant composition during useunder oxidizing or other service conditions regardless of the color orother properties of the resulting lubricant composition.

In some embodiments, the epoxide compound does not negatively affect thetotal base number of the lubricant composition. Alternatively, theepoxide compound may improve the TBN of the lubricant composition by, at0.5, 1, 1.5, 2, 2.5, 3, 3.5, 4, 4.5, 5, 10, or 15, mg KOH/g of epoxidecompound. The TBN value of the lubricant composition can be determinedaccording to ASTM D2896 and/or ASTM D4739 as will be described below.

In certain embodiments, the epoxide compound is monomeric. The term“monomeric” is intended to indicate that the subject compound does notinclude more than three, more than two, or more than one, repeatingmonomer units bonded to one another. Alternatively, the term monomericmay refer to compounds that do not include any repeating monomer units.In other words, the term “monomeric” is intended to exclude compoundswhich are either oligomeric or polymeric. In certain embodiments, themonomeric epoxide compound excludes oils or alkyl fatty acid esterswhich have been epoxidized to include one or more oxirane rings, such asepoxidized vegetable oils. Alternatively, the lubricant composition oradditive package may include less than 5, 4, 3, 2, 1, 0.5, 0.1, or 0.01,wt. %, of an epoxidized fatty acid ester or epoxidized oil based on atotal weight of said lubricant composition. As used herein, the term“epoxidized oil” refers to a natural oil which was epoxidized to includeat least 1, at least 2, at least 3, at least 4, at least 5, at least 6,at least 7, at least 8, or at least 9, epoxide groups per moleculeand/or has an epoxide equivalent weight of greater than 200, 250, 300,or 350. As used herein, the term “epoxidized fatty acid ester” refers toa natural fatty acid ester or acid that includes at least 1, at least 2,at least 3, at least 4, at least 5, at least 6, at least 7, at least 8,or at least 9, epoxide groups per molecule and/or has a epoxideequivalent weight of greater than 200, 250, 300, or 350. As used herein,the term “natural” refers to compounds which are naturally-occurring.

The epoxide compound may have a boiling point of at least 50, 60, 70,80, 90, 100, 110, 120, 130, 140, or 150, ° C., at 1 atmosphere ofpressure. Alternatively, the epoxide compound has a boiling point offrom 50 to 450, 55 to 450, 65 to 450, 75 to 450, 85 to 450, 100 to 450,115 to 450, 125 to 450, 135 to 450, 150 to 450, or from 200 to 400, °C., at 1 atmosphere of pressure. Furthermore, in certain embodiments,the epoxide compound is a liquid at a steady state temperature of 50° C.and a steady state pressure of 1 atmosphere of pressure.

The epoxide compound may have a flash point of from 25 to 250, 50 to250, 65 to 250, 75 to 250, 100 to 250, or from 115 to 250, ° C. at 1atmosphere of pressure. Alternatively, the epoxide compound may have aflash point of at least 25, 35, 45, 55, 65, 75, 85, 95, 105, 115, 125,or 135, ° C. at 1 atmosphere of pressure.

The amount of the epoxide compound included in the lubricant compositionranges from 0.01 to 8, 0.05 to 5, 0.1 to 2, 0.1 to 1.5, 0.3 to 1.2, 0.4to 1, 0.1 to 1, 0.1 to 0.8, or 0.2 to 0.7, wt. %, based on the totalweight of the lubricant composition. The epoxide compound may beincluded in the additive package in an amount of from 0.5 to 90, 1 to50, 1 to 30, or 5 to 25, wt. %, based on the total weight of theadditive package. The lubricant composition and/or additive package mayinclude mixtures of two or more different epoxide compounds.

In certain embodiments, the epoxide compound is included in thelubricant composition in an amount sufficient to provide from 0.01 to 5,0.01 to 4.5, 0.01 to 4, 0.01 to 3.5, 0.01 to 3, 0.01 to 2.5, 0.01 to 2,0.01 to 1.5, 0.01 to 1, 0.1 to 0.9, 0.2 to 0.8, or 0.3 to 0.7, wt. % ofoxirane oxygen, based on total weight of the lubricant composition.

The epoxide compound may be prepared using various methods as will beappreciated by one of ordinary skill in the art. For example, theepoxide compound may be prepared by the epoxidation of an allyl ether,α,β-unsaturated amide to the corresponding glycidyl ether, glycidicester, or glycidic amide. Alternatively, an olefin may be epoxidizedwith hydrogen peroxide and an organic peracid to produce the epoxidecompound. Alternatively, the olefin can be epoxidized in the presence ofa transition metal catalyst and a co-oxidant to form the epoxidecompound. Suitable co-oxidants include hydrogen peroxide, tert-butylhydroperoxide, iodosylbenzene, sodium hypocholorite, and the like.Alternatively, glycidic esters may be prepared by Darzens condensationof an α-halo ester and an aldehyde or ketone, in the presence of a base.

In some embodiments, the lubricant composition and/or additive packageis free of, or contains less than 5, 3, 1, 0.5, 0.1, or 0.05, wt. % ofan epoxide reaction catalyst, based on the total weight of the lubricantcomposition. The epoxide reaction catalyst may be a metal salt, such asa metallic salt of fatty acids, naphthenates, phenolates, alcoholates,carboxylates, and the corresponding thio analogues, sulfonates, andsulphinates. The epoxide reaction catalyst may also refer to calciumcetyl alcoholate, barium isoamyl thiiphenolate, calcium naphthnate, andmetal salts of alkyl substituted benzene sulphonic acid. In someembodiments, the epoxide reaction catalyst is defined as a componentthat catalyzes the reaction of the epoxide compound with an additionalcomponent in the lubricant composition at a temperature less than 100,80, or, 60, ° C. The additional component may include, but is notlimited to, any compound described in this specification other than theepoxide reaction catalyst and the epoxide compound. For example, theadditional component referred to above may be a dispersant, an antiwearadditive, an antioxidant, or a component that affects the total basenumber of the lubricant composition.

Conventional uses of epoxide compounds in lubricant compositions involveforming a reaction product between a conventional dispersant and aconventional epoxide compound. In these applications, the conventionalepoxide compound is consumed by chemical reactions such that theultimately formed lubricant composition does not contain appreciableamounts of the conventional epoxide compound in an unreacted state. Theconventional epoxide compound may react via an addition reaction suchthat the addition of one or more small molecules to the lubricantcomposition may cause the epoxide group of the conventional epoxidecompound to ring-open without eliminating or cleaving any part of theconventional epoxide compound.

In such conventional uses, more than 50 wt. % of the conventionalepoxide compound is typically reacted with the conventional dispersantsor other compounds based on the total weight of the conventional epoxidecompound in the lubricant composition prior to the reaction. Incontrast, the inventive lubricant compositions may contain a significantamount of the epoxide compound in an unreacted state. In certainembodiments, at least 50, 60, 70, 80 or, 90, wt. % of the epoxidecompound remains unreacted in the lubricant composition based on a totalweight of the epoxide compound utilized to form the lubricantcomposition prior to any reaction in the lubricant composition.Alternatively, at least 95, 96, 97, 98, or 99, wt. %, of the epoxidecompound remains unreacted in the lubricant composition based on a totalweight of the epoxide compound prior to any reaction in the lubricantcomposition.

The phrase “prior to any reaction in the lubricant composition” refersto the basis of the amount of the epoxide compound in the lubricantcomposition. This phrase does not require that the epoxide compoundreacts with other components in the lubricant composition, i.e., 100 wt.% of the epoxide compound may remain unreacted in the lubricantcomposition based on a total weight of the epoxide compound prior to anyreaction in the lubricant composition.

The percentage of the epoxide compound that remains unreacted istypically determined after all of the components which are present inthe lubricant composition reach equilibrium with one another. The timeperiod necessary to reach equilibrium in the lubricant composition mayvary widely. For example, the amount of time necessary to reachequilibrium may range from a single minute to many days, or even weeks.The percentage of the epoxide compound that remains unreacted in thelubricant composition may be determined after 1 minute, 1 hour, 5 hours,12 hours, 1 day, 2 days, 3 days, 1 week, 1 month, 6 months, or 1 year.

In certain embodiments, the lubricant composition includes less than 10,5, 1, 0.5, 0.1, 0.01, 0.001, or 0.0001, wt. %, of compounds which wouldreact with the epoxide compound at a temperature less than 150, lessthan 125, less than 100, or less than 80, ° C., based on a total weightof the lubricant composition. Exemplary types of compounds which mayreact with the epoxide compound at a temperature less than 100° C.include acids, amine curing agents, anyhydrides, triazoles, and/oroxides. In certain embodiments, the lubricant composition may include acollective amount of acids, amine curing agents, anhydrides, triazoles,and/or oxides which is less than 5, 3, 1, 0.5, or 0.1, wt. % based on atotal weight of the lubricant composition. Alternatively, the lubricantcomposition may include a collective amount of acids, amine curingagents, anhydrides, triazoles, and/or oxides which is less than 0.01,0.001, or 0.0001, wt. %, based on the total weight of the lubricantcomposition. Alternatively still, the lubricant composition may be freeof acids, amine curing agents, anhydrides, triazoles, and/or oxides.

The term “acids” may include both traditional acids and Lewis acids. Forexample, acids include carboxylic acids, such as lactic acid andhydracylic acid; alkylated succinic acids; alkylaromatic sulfonic acids;and fatty acids. Exemplary Lewis acids include alkyl aluminates; alkyltitanates; molybdenumates, such as molybdenum thiocarbamates andmolybdenum carbamates; and molybdenum sulfides.

Anhydrides are exemplified by alkylated succinic anhydrides andacrylates. Triazoles may be represented by benzotriazoles andderivatives thereof; tolutriazole and derivatives thereof;2-mercaptobenzothiazole, 2,5-dimercaptothiadiazole,4,4′-methylene-bis-benzotriazole, 4,5,6,7-tetrahydro-benzotriazole, andsalts thereof. Oxides may be represented by alkylene oxides, such asethylene oxide and propylene oxide; metal oxides; alkoxylated alcohols;alkoxylated amines; or alkoxylated esters.

In other conventional uses, conventional epoxide compounds undergotribopolymerization in lubricant compositions to form protectivelubricating films. In the tribopolymerization process, polymer-formersare adsorbed on a solid surface and polymerize under rubbing conditionsto form organic polymeric films directly on the rubbing surface. In suchconventional uses, more than 50 wt. % of the conventional epoxidecompound is typically reacted via tribopolymerization. In contrast, theinventive lubricant compositions may contain a significant amount of theepoxide compound that does not react via tribopolymerization. In certainembodiments, at least 50, 60, 70, 80, or 90, wt. %, of the epoxidecompound does not react via tribopolymerization in the lubricantcomposition at a temperature less than 100, 80, or 60, ° C., based onthe total weight of epoxide compound utilized to form the lubricantcomposition. Alternatively, at least 95, 96, 97, 98, or 99, wt. %, ofthe epoxide compound does not react via tribopolymerization in thelubricant composition at a temperature less than 100, 80, or 60, ° C.,based on a total weight of the epoxide compound in the lubricantcomposition.

As described above, the epoxide compound may be combined with at leastone amine compound in the lubricant composition or additive package. Itshould be appreciated that mixtures of different amine compounds mayalso be combined with the epoxide compound in the lubricant compositionand/or additive package. If utilized, the lubricant composition includesthe amine compound in an amount of from 0.1 to 25, 0.1 to 20, 0.1 to 15,or 0.1 to 10, wt. %, based on the total weight of the lubricantcomposition. Alternatively, the lubricant composition may include theamine compound in an amount of from 0.5 to 5, 1 to 3, or 1 to 2, wt. %,based on the total weight of the lubricant composition.

The amine compound does not substantially react with the epoxidecompound to form a salt. The absence of salt formation is evidenced bythe lack of a chemical shift in the NMR spectra of the epoxide compoundand the amine compound when they are combined in the lubricantcomposition and/or additive package. In other words, at least 50, 60,70, 80, 90, 95, or 99, wt. %, of the amine compound remains unreactedafter the lubricant composition and/or additive package reachesequilibrium.

In certain embodiments, the amine compound has a TBN value of at least80 mg KOH/g when tested according to ASTM D4739. Alternatively, theamine compound has a TBN value of at least 90, at least 100, at least110, at least 120, at least 130, at least 140, at least 150, or at least160, mg KOH/g, when tested according to ASTM D4739. Alternatively still,the amine compound may have a TBN value of from 80 to 200, 90 to 190,100 to 180, or 100 to 150, mg KOH g, when tested according to ASTMD4739.

In some embodiments, the amine compound does not negatively affect thetotal base number of the lubricant composition. Alternatively, the aminecompound may improve the TBN of the lubricant composition by, at least0.5, at least 1, at least 1.5, at least 2, at least 2.5, at least 3, atleast 3.5, at least 4, at least 4.5, at least 5, at least 10, or atleast 15, mg KOH/g of the amine compound. The TBN value of the lubricantcomposition can be determined according to ASTM D2896.

If the amine compound is included in the additive package, the additivepackage includes the amine compound in an amount of from 0.1 to 50 wt.%, based on the total weight of the additive package. Alternatively, theadditive package may include the amine compound in an amount of from 1to 25, 0.1 to 15, 1 to 10, 0.1 to 8, or 1 to 5, wt. %, based on thetotal weight of the additive package. Combinations of various aminecompounds are also contemplated.

The amine compound includes at least one nitrogen atom. Furthermore, insome configurations, the amine compound does not include triazoles,triazines, or similar compounds where there are three or more nitrogenatoms in the body of a cyclic ring. The amine compound may be aliphatic.

In some embodiments, the amine compound consists of, or consistsessentially of, hydrogen, carbon, nitrogen, and oxygen. Alternatively,the amine compound may consist of, or consist essentially of, hydrogen,carbon, and nitrogen. In the context of the amine compound, the phrase“consist essentially of” refers to compounds where at least 95 mole % ofthe amine compound are the recited atoms (i.e., hydrogen, carbon,nitrogen, and oxygen; or hydrogen, carbon, and nitrogen). For example,if the amine compound consists essentially of hydrogen, carbon,nitrogen, and oxygen, at least 95 mole % of the amine compound ishydrogen, carbon, nitrogen, and oxygen. In certain configurations, atleast 96, at least 97, at least 98, at least 99, or at least 99.9, mole%, of the amine compound are hydrogen, carbon, nitrogen and oxygen, or,in other embodiments, are carbon, nitrogen, and hydrogen.

The amine compound may consist of covalent bonds. The phrase “consist ofcovalent bonds” is intended to exclude those compounds which bond to theamine compound through an ionic association with one or more ionic atomsor compounds. That is, in configurations where the amine compoundconsists of covalent bonds, the amine compound excludes salts of aminecompounds, for example, phosphate amine salts and ammonium salts. Assuch, in certain embodiments, the lubricant composition is free of asalt of the amine compound. More specifically, the lubricant compositionmay be free of a phosphate amine salt, ammonium salt, and/or aminesulfate salt.

The amine compound may be a monomeric acyclic amine compound having aweight average molecular weight of less than 500. Alternatively, themonomeric acyclic amine compound may have a weight average molecularweight of less than 450, less than 400, less than 350, less than 300,less than 250, less than 200, or less than 150. Alternatively still, theamine compound may have a weight average molecular weight of at least30, at least 50, at least 75, at least 100, at least 150, at least 200,or at least 250.

The term “acyclic” is intended to refer to compounds which are free fromany cyclic structures and to exclude aromatic structures. For example,the monomeric acyclic amine compound does not include compounds having aring having at least three atoms bonded together in a cyclic structureand those compounds including benzyl, phenyl, or triazole groups.

The monomeric acyclic amine compound may be exemplified by generalformula (X):

where each R¹³ is independently a hydrogen atom or a hydrocarbyl group.The hydrocarbyl group designated by R¹³ may have the same meaning as Rdescribed above with respect to general formula (I). For example, eachR¹³ may independently be a hydrocarbyl group including an alcohol group,an amino group, an amide group, an ether group, or an ester group. Themonomeric acyclic amine includes monoamines and polyamines (includingtwo or more amine groups).

In certain embodiments, at least one group designated by R¹³ isunsubstituted. Alternatively, two or three groups designated by R¹³ areunsubstituted. Alternatively still, it is contemplated that one, two, orthree groups designated by R¹³ are substituted. As outlined above withrespect to R in general formula (I), the term “substituted” indicatesthat the designated group includes at least one substituent group,and/or that the designated group includes at least one heteroatom orheterogroup.

Exemplary alkyl R¹³ groups may be independently selected from methyl,ethyl, n-propyl, n-butyl, sec-butyl, tert-butyl, n-hexyl, n-octyl,2-ethylhexyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl,n-tetradecyl, n-hexadecyl, or n-octadecyl.

Exemplary monomeric acyclic amine compounds include, but are not limitedto, primary, secondary, and tertiary amines, such as:

-   methylamine:

H₂N—CH₃

-   ethanolamine:

-   dimethylamine:

-   methylethanolamine:

-   trimethylamine:

-   bis(2-ethylhexyl)amine:

-   ditridecylamine:

The monomeric acyclic amine compound may alternatively be one or moreother primary amines such as ethylamine, n-propylamine, isopropylamine,n-butylamine, isobutylamine, sec-butylamine, tert-butylamine,pentylamine, and hexylamine; primary amines of the formulas:CH₃—O—C₂H₄—NH₂, C₂H₅—O—C₂H₄—NH₂, CH₃—O—C₃H₆—NH₂, C₂H₅—O—C₃H₆—NH₂,C₄H₉—O—C₄H₈—NH₂, HO—C₂H₄—NH₂, HO—C₃H₆—NH₂ and HO—C₄H₈—NH₂; secondaryamines, for example diethylamine, methylethylamine, di-n-propylamine,diisopropylamine, diisobutylamine, di-sec-butylamine,di-tert-butylamine, dipentylamine, dihexylamine; and also secondaryamines of the formulas: (CH₃—O—C₂H₄)₂NH, (C₂H₅—O—C₂H₄)₂NH,(CH₃—O—C₃H₆)₂NH, (C₂H₅—O—C₃H₆)₂NH, (n-C₄H₉—O—C₄H₈)₂NH, (HO—C₂H₄)₂NH,(HO—C₃H₆)₂NH and (HO—C₄H₈)₂NH; and polyamines, such asn-propylenediamine, 1,4-butanediamine, 1,6-hexanediamine,diethylenetriamine, triethylenetetramine and tetraethylenepentamines,and also their alkylation products, for example3-(dimethylamino)-n-propylamine, N,N-dimethylethylenediamine,N,N-diethylethylenediamine, and N,N,N′,N′-tetramethyldiethylenetriamine.

Alternatively, the amine compound may be a monomeric cyclic aminecompound. The monomeric cyclic amine compound may have a weight averagemolecular weight of from 100 to 1200, 200 to 800, or 200 to 600.Alternatively, the monomeric cyclic amine compound may have a weightaverage molecular weight of less than 500, or at least 50. In someembodiments, the monomeric cyclic amine compound is free from aromaticgroups, such as phenyl and benzyl rings. In other embodiments, themonomeric cyclic amine compound is aliphatic.

The monomeric cyclic amine compound may include two or fewer nitrogenatoms per molecule. Alternatively, the monomeric cyclic amine compoundmay include only one nitrogen per molecule. The phrase “nitrogen permolecule” refers to the total number of nitrogen atoms in the entiremolecule, including the body of the molecule and any substituent groups.In certain embodiments, the monomeric cyclic amine compound includes oneor two nitrogen atoms in the cyclic ring of the monomeric cyclic aminecompound.

The monomeric cyclic amine compound may be exemplified by the generalformula (XI):

orgeneral formula (XII):

In general formulas (XI) and (XII), Y represents the type and number ofatoms necessary to complete the cyclic ring of general formulas (XI) or(XII). The ring designated by Y may include from 2 to 20, 3 to 15, 5 to15, or 5 to 10, carbon atoms. The ring designated by Y may be asubstituted or unsubstituted, branched or unbranched, divalenthydrocarbon group that includes one or more hetero atoms, such asoxygen, or sulfur, and may include one or more heterogroups. In additionto including heteroatoms and/or heterogroups, the ring designated by Ymay include one or more hydrocarbyl substituent groups, as describedabove with respect to R in general formula (I). In certain embodiments,the ring designated by Y is free from nitrogen heteroatoms, or free fromany heteroatoms. The heteroatoms, heterogroups, and/or substituentgroups may be bonded to different atoms in the divalent hydrocarbongroup designated by Y. The substituent nitrogen atom in general formula(XII) may be bonded to one or more hydrogen atoms, or may be bonded toone or two hydrocarbyl groups.

In formula (XI), R¹⁴ is a hydrogen atom or a hydrocarbyl group. Thehydrocarbyl group designated by R¹⁴ may have the same meaning as Rdescribed above with respect to formula (I). For example, R¹⁴ may be analcohol group, an amino group, an alkyl group, an amide group, an ethergroup, or an ester group. R¹⁴ may have 1 to 50, 1 to 25, 1 to 17, 1 to15, 1 to 12, 1 to 8, 1 to 6, or 1 to 4, carbon atoms. R¹⁴ may bestraight or branched. For example, each R¹² may be an alcohol group,amino group, alkyl group, amide group, ether group, or ester grouphaving 1 to 50 carbon atoms, with the designated functional group(alcohol, etc.), heteroatom, or heterogroup bonded at various positionson the carbon chain. The substituent nitrogen atom in general formula(XII) may be bonded to one or more hydrogen atoms, or may be bonded toone or two hydrocarbyl groups, such as those described above withrespect to R¹⁴.

In one more specific embodiment, the monomeric cyclic amine compound maybe exemplified by general formula (XIII):

In general formula (XIII), each R¹⁵ is independently a hydrogen atom ora hydrocarbyl group having from 1 to 17 carbon atoms. The hydrocarbylgroup designated by R¹⁵ may have the same meaning as R in generalformula (I). For example, each R¹⁵ may independently be substituted withan alcohol group, an amino group, an amide group, an ether group, or anester group. Each R¹⁵ may independently have from 1 to 17, 1 to 15, 1 to12, 1 to 8, 1 to 6, or 1 to 4, carbon atoms. In certain embodiments, atleast one group designated by R¹⁵ is unsubstituted. Alternatively, atleast two, three, four, five, or six groups designated by R¹⁵ areunsubstituted. Alternatively still, it is contemplated that one, two,three, four, five, or six groups designated by R¹⁵ are substituted. Forexample, each R¹⁵ may be an alcohol group, amino group, alkyl group,amide group, ether group, or ester group having 1 to 17 carbon atoms,with the designated functional group (alcohol, etc) bonded at variouspositions on the carbon chain.

Exemplary monomeric cyclic amine compounds include:

-   cyclopentylamine:

-   cyclohexylamine:

-   aziridine:

-   piperidine:

-   n-methylpiperidine:

In some embodiments, the monomeric acyclic amine compound or themonomeric cyclic amine compound may be a sterically hindered aminecompound. In one or more embodiments, the sterically hindered aminecompound may have a weight average molecular weight of from 100 to 1200.Alternatively, the sterically hindered amine compound may have a weightaverage molecular weight of from 200 to 800, or from 200 to 600.Alternatively still, the sterically hindered amine compound may have aweight average molecular weight of less than 500.

As used herein, the term “sterically hindered amine compound” means anorganic molecule having fewer than two hydrogen atoms bonded to at leastone alpha-carbon with reference to a secondary or tertiary nitrogenatom. In other embodiments, the term “sterically hindered aminecompound” means an organic molecule having no hydrogen atoms bonded toat least one alpha-carbon with reference to a secondary or tertiarynitrogen atom. In still other embodiments, the term “sterically hinderedamine compound” means an organic molecule having no hydrogen atomsbonded to each of at least two alpha-carbons with reference to asecondary or tertiary nitrogen atom.

The sterically hindered amine compound may have general formula (XIV) or(XV):

In general formula (XIV), each R¹⁶ is independently a hydrogen atom or ahydrocarbyl group having from 1 to 17 carbon atoms, wherein at least twoof R¹⁶ are an alkyl group in one molecule; and R¹⁷ is independently ahydrogen atom or a hydrocarbyl group having from 1 to 17 carbon atoms.In general formula (XV), each R¹⁸ is independently a hydrogen atom or ahydrocarbyl group having from 1 to 17 carbon atoms, wherein at least twoof R¹⁸ are an alkyl group, and each R¹⁹ is independently a hydrogen atomor a hydrocarbyl group having from 1 to 17 carbon atoms.

The groups designated by R¹⁶, R¹⁷, R¹⁸, and R¹⁹ may have the samemeaning as R described above with respect to general formula (I). Forexample, each R¹⁶, R¹⁷, R¹⁸, and R¹⁹ may independently substituted withan alcohol group, an amide group, an ether group, or an ester group, andeach R¹⁶, R¹⁷, R¹⁸, and R¹⁹ may independently have from 1 to 17, 1 to15, 1 to 12, 1 to 8, 1 to 6, or 1 to 4, carbon atoms.

In certain embodiments, at least one group designated by R¹⁶, R¹⁷, R¹⁸,and R¹⁹ is unsubstituted. Alternatively, at least two, three, four,five, or six groups designated by R¹⁶, R¹⁷, R¹⁸, and R¹⁹ areunsubstituted. In other embodiments, every group designated by R¹⁶, R¹⁷,R¹⁸, and R¹⁹ is unsubstituted. Alternatively still, it is contemplatedthat one, two, three, four, five, or six groups designated by R¹⁶, R¹⁷,R¹⁸, and R¹⁹ are substituted.

Exemplary R¹⁶, R¹⁷, R¹⁸, and R¹⁹ groups may be independently selectedfrom methyl, ethyl, n-propyl, n-butyl, sec-butyl, tert-butyl, n-hexyl,n-octyl, 2-ethylhexyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl,n-tridecyl, n-tetradecyl, n-hexadecyl, or n-octadecyl.

In general formula (XIV), at least two, at least three, or all fourgroups, designated by R¹⁶ are each independently an alkyl group.Similarly, in general formula (XV), at least two groups designated byR¹⁸ are an alkyl group. Alternatively, at least three, or all fourgroups, designated by R¹⁸ are an alkyl group.

The sterically hindered amine compound of general formula (XIV) may beexemplified by the following compounds:

-   2,2,6,6-tetramethyl-4-octylpiperidine:

-   2,2,6,6-tetramethyl-4-decylpiperidine:

-   2,2,6,6-tetramethyl-4-butylpiperidine:

-   2,2,6,6-tetramethyl-4-hexadecylpiperidine:

The sterically hindered amine compound of general formula (XV) isacyclic. The term “acyclic” is intended to mean that the stericallyhindered amine compound of general formula (XV) is free from any cyclicstructures and aromatic structures. The sterically hindered aminecompound of general formula (XV) can be exemplified by:

-   N-tert-butyl-2-ethyl-N-methyl-hexan-1-amine:

-   tert-amyl-tert-butylamine:

-   N-tert-butylheptan-2-amine:

The sterically hindered amine compound may alternatively be exemplifiedby the general formula (XVI):

In general formula (XVI), each R¹⁶ and R¹⁷ are as described above,wherein at least three of R¹⁶ are each independently an alkyl group. Thesterically hindered amine compound of general formula (XVI) may beexemplified by the following compounds:

-   (1,2,2,6,6-pentamethyl-4-piperidyl)octanoate:

-   (1,2,2,6,6-pentamethyl-4-piperidyl)decanoate:

-   (1,2,2,6,6-pentamethyl-4-piperidyl)dodecanoate:

-   (2,2,6,6-tetramethyl-4-piperidyl)dodecanoate:

The sterically hindered amine compound may include a single ester group.However, the sterically hindered amine compound may alternatively befree from ester groups. In certain embodiments, the sterically hinderedamine compound may include at least one, or only one, piperidine ring.

The epoxide compound and the amine compound may be provided in thelubricant composition or additive package in an amount such that 1 partof oxirane oxygen is provided for every 1 to 20 parts nitrogen in theamine compound. Alternatively, the epoxide compound and the aminecompound may be provided in an amount such that 1 part of oxirane oxygenis provided for every 1 to 15, 1 to 10, or 1 to 5, parts nitrogen, inthe amine compound within the lubricant composition or additive package.

In one specific embodiment, the lubricant composition may consist, orconsist essentially of, a base oil, the epoxide compound, and the aminecompound. It is also contemplated that the lubricant composition mayconsist of, or consist essentially of, the base oil, the epoxidecompound, and the amine compound, in addition to one or more ofadditives that do not materially affect the functionality or performanceof the epoxide compound. For example, compounds that materially affectthe overall performance of the lubricant composition may includecompounds which negatively impact the TBN boost, the lubricity, thefluoropolymer seal compatibility, the corrosion inhibition, or theacidity of the lubricant composition.

In other embodiments, the additive package may consist, or consistessentially of, the epoxide compound and the amine compound. It is alsocontemplated that the additive package may consist of, or consistessentially of, the epoxide compound, and the amine compound in additionto one or more of additives that do not compromise the functionality orperformance of the epoxide compound. When used in reference to theadditive package, the term “consisting essentially of” refers to theadditive package being free of compounds that materially affect theoverall performance of the additive package. For example, compounds thatmaterially affect the overall performance of the additive package mayinclude compounds which negatively impact the TBN boost, the lubricity,the fluoropolymer seal compatibility, the corrosion inhibition, or theacidity of the additive package.

The lubricant composition may include a base oil. The base oil isclassified in accordance with the American Petroleum Institute (API)Base Oil Interchangeability Guidelines. In other words, the base oil maybe further described as one or more of five types of base oils: Group I(sulphur content >0.03 wt. %, and/or <90 wt. % saturates, viscosityindex 80-119); Group II (sulphur content less than or equal to 0.03 wt.%, and greater than or equal to 90 wt. % saturates, viscosity index80-119); Group III (sulphur content less than or equal to 0.03 wt. %,and greater than or equal to 90 wt. % saturates, viscosity index greaterthan or equal to 119); Group IV (all polyalphaolefins (PAO's)); andGroup V (all others not included in Groups I, II, III, or IV).

In some embodiments, the base oil is selected from the group of APIGroup I base oils; API Group II base oils; API Group III base oils; APIGroup IV base oils; API Group V base oils; and combinations thereof. Inone specific embodiment, the base oil includes API Group II base oils.

The base oil may have a viscosity of from 1 to 50, 1 to 40, 1 to 30, 1to 25, or 1 to 20, cSt, when tested according to ASTM D445 at 100° C.Alternatively, the viscosity of the base oil may range from 3 to 17, or5 to 14, cSt, when tested according to ASTM D445 at 100° C.

The base oil may be further defined as a crankcase lubricant oil forspark-ignited and compression-ignited internal combustion engines,including automobile and truck engines, two-cycle engines, aviationpiston engines, marine engines, and railroad diesel engines.Alternatively, the base oil can be further defined as an oil to be usedin gas engines, diesel engines, stationary power engines, and turbines.The base oil may be further defined as heavy or light duty engine oil.

In still other embodiments, the base oil may be further defined assynthetic oil that includes one or more alkylene oxide polymers andinterpolymers, and derivatives thereof. The terminal hydroxyl groups ofthe alkylene oxide polymers may be modified by esterification,etherification, or similar reactions. Typically, these synthetic oilsare prepared through polymerization of ethylene oxide or propylene oxideto form polyoxyalkylene polymers which can be further reacted to formthe synthetic oil. For example, alkyl and aryl ethers of thesepolyoxyalkylene polymers may be used. For example,methylpolyisopropylene glycol ether having a weight average molecularweight of 1000; diphenyl ether of polyethylene glycol having a molecularweight of 500-1000; or diethyl ether of polypropylene glycol having aweight average molecular weight of 1,000-1500 and/or mono- andpolycarboxylic esters thereof, such as acetic acid esters, mixed C₃-C₈fatty acid esters, and the C₁₃ oxo acid diester of tetraethylene glycolmay also be utilized as the base oil. Alternatively, the base oil mayinclude a substantially inert, normally liquid, organic diluent, such asmineral oil, naptha, benzene, toluene, or xylene.

The base oil may include less than 90, less than 80, less than 70, lessthan 60, less than 50, less than 40, less than 30, less than 20, lessthan 10, less than 5, less than 3, less than 1, or be free from, anestolide compound (i.e., a compound including one or more estolidegroups), based on the total weight of the lubricant composition.

The base oil may be present in the lubricant composition in an amount offrom 1 to 99.9, 50 to 99.9, 60 to 99.9, 70 to 99.9, 80 to 99.9, 90 to99.9, 75 to 95, 80 to 90, or 85 to 95, wt. %, based on the total weightof the lubricant composition. Alternatively, the base oil may be presentin the lubricant composition in amounts of greater than 1, 10, 20, 30,40, 50, 60, 70, 75, 80, 85, 90, 95, 98, or 99, wt. %, based on the totalweight of the lubricant composition. In various embodiments, the amountof base oil in a fully formulated lubricant composition (includingdiluents or carrier oils present) ranges from 50 to 99, 60 to 90, 80 to99.5, 85 to 96, or 90 to 95, wt. %, based on the total weight of thelubricant composition. Alternatively, the base oil may be present in thelubricant composition in an amount of from 0.1 to 50, 1 to 25, or 1 to15, wt. %, based on the total weight of the lubricant composition. Invarious embodiments, the amount of base oil in an additive package, ifincluded, (including diluents or carrier oils present) ranges from 0.1to 50, 1 to 25, or 1 to 15, wt. %, based on the total weight of theadditive package.

In one or more embodiments, the lubricant composition may be classifiedas a low SAPS lubricant having a sulfated ash content of no more than 3,2, 1, or 0.5, wt. %, based on the total weight of the lubricantcomposition. “SAPS” refers to sulfated ash, phosphorous and sulfur.

The lubricant composition may have a TBN value of at least 1, at least3, at least 5, at least 7, at least 9, mg KOH/g of lubricantcomposition, when tested according to ASTM D2896. Alternatively, thelubricant composition has a TBN value of from 3 to 100, 3 to 75, 50 to90, 3 to 45, 3 to 35, 3 to 25, 3 to 15, or 9 to 12, mg KOH/g oflubricant composition, when tested according to ASTM D2896.

In certain embodiments, the lubricant composition is a multigradelubricant composition identified by the viscometric descriptor SAE15WX,SAE 10WX, SAE 5WX or SAE OWX, where X is 8, 12, 16, 20, 30, 40, or 50.The characteristics of one or more of the different viscometric gradescan be found in the SAE J300 classification.

The lubricant composition may have a phosphorus content of less than1500, less than 1200, less than 1000, less than 800, less than 600, lessthan 400, less than 300, less than 200, or less than 100, or 0, ppm, asmeasured according to the ASTM D5185 standard, or as measured accordingto the ASTM D4951 standard. The lubricant composition may have a sulfurcontent of less than 3000, less than 2500, less than 2000, less than1500, less than 1200, less than 1000, less than 700, less than 500, lessthan 300, or less than 100, ppm, as measured according to the ASTM D5185standard, or as measured according to the ASTM D4951 standard.

Alternatively, the lubricant composition may have a phosphorous contentof from 1 to 1000, 1 to 800, 100 to 700, or 100 to 600, ppm, as measuredaccording to the ASTM D5185 standard.

The lubricant composition may be free from, or substantially free from,a carboxylic acid ester and/or phosphate ester. For example, thelubricant composition may include less than 20, less than 15, less than10, less than 5, less than 3, less than 1, less than 0.5, or less than0.1, wt. %, carboxylic acid ester and/or phosphate ester. The carboxylicacid ester and/or phosphate ester may be included as conventional baseoil in water-reactive functional fluids. The lubricant composition maybe free from a carboxylic acid ester base oil and/or phosphate esterbase oil, which are liquid at a steady state temperature of 25° C. and asteady state pressure of 1 atmosphere.

The lubricant composition may be unreactive with water. By unreactivewith water, it is meant that less than 5, 4, 3, 2, 1, 0.5, or 0.1,wt.,%, of the lubricant composition reacts with water at 1 atmosphere ofpressure and 25° C.

In various embodiments, the lubricant composition is substantially freeof water, e.g., the lubricant composition includes less than 5, lessthan 4, less than 3, less than 2, less than 1, less than 0.5, or lessthan 0.1, wt. %, of water, based on the total weight of the lubricantcomposition. Alternatively, the lubricant composition may be completelyfree of water.

The lubricant composition may be a lubricant composition, such as acrankcase lubricant composition, having a total additive treat rate ofat least 3, at least 4, at least 5, at least 6, at least 7, or at least8, wt. %, based on a total weight of the lubricant composition.Alternatively, the lubricant composition may have a total additive treatrate ranging from 3 to 20, 4 to 18, 5 to 16, or 6 to 14, wt. %, based ona total weight of the lubricant composition. The term “total additivetreat rate” refers to the total weight percentage of additives includedin the lubricant composition. The additives accounted for in the totaladditive treat rate include, but are not limited to, epoxide compounds,amine compounds, dispersants, detergents, aminic antioxidants, phenolicantioxidants, anti-foam additives, antiwear additives, pour pointdepressants, viscosity modifiers, and combinations thereof. In certainembodiments, an additive is any compound in the lubricant compositionother than the base oil. In other words, the total additive treat ratecalculation does not account for the base oil as an additive.

The additive package may include, but is not limited to, epoxidecompounds, amine compounds, dispersants, detergents, aminicantioxidants, phenolic antioxidants, anti-foam additives, antiwearadditives, pour point depressants, viscosity modifiers, and combinationsthereof. The lubricant composition may include the additive package inamount of at least 3, at least 4, at least 5, at least 6, at least 7, orat least 8, wt. %, based on a total weight of the lubricant composition.Alternatively, the lubricant composition may include the additivepackage in an amount of from 3 to 20, 4 to 18, 5 to 16, or 6 to 14, wt.%, based on a total weight of the lubricant composition. In someembodiments, the additive package does not account for the weight of thebase oil as an additive. Although not required, the additive packageincludes all compounds in the lubricant composition other than the baseoil. However, it is to be appreciated that certain individual componentscan be independently and individually added to the lubricant compositionseparate from the addition of the additive package to the lubricantcomposition, yet still be considered part of the additive package oncethe additive which was individually added into the lubricant compositionis present in the lubricant composition along with the other additives.

The additive package refers to the collective amount of the epoxidecompounds, amine compounds, dispersants, detergents, aminicantioxidants, phenolic antioxidants, anti-foam additives, antiwearadditives, pour point depressants, viscosity modifiers, or combinationsthereof in a solution, mixture, concentrate, or blend, such as thelubricant composition. In some embodiments, the term “additive package”does not require that these additives are physically packaged togetheror blended together before addition to the base oil. Thus, a base oilwhich includes the epoxide compound and the dispersant, each added tothe base oil separately, could be interpreted to be a lubricantcomposition that includes an additive package that includes the epoxidecompound and the dispersant. In other embodiments, the additive packagerefers to a blend of the epoxide compounds, amine compounds,dispersants, detergents, aminic antioxidants, phenolic antioxidants,anti-foam additives, antiwear additives, pour point depressants,viscosity modifiers, or combinations thereof. The additive package maybe blended into the base oil to make the lubricant composition.

The additive package may be formulated to provide the desiredconcentration in the lubricant composition when the additive package iscombined with a predetermined amount of base oil. It is to beappreciated that most references to the lubricant composition throughoutthis disclosure also apply to the description of the additive package.For example, it is to be appreciated that the additive package mayinclude, or exclude, the same components as the lubricant composition,albeit in different amounts.

In one embodiment, the lubricant composition passes ASTM D4951 forphosphorus content. ASTM D4951 is a standard test method fordetermination of additive elements in lubricant compositions byinductively coupled plasma atomic emission spectrometry (ICP-OES).

In another embodiment, the lubricant composition passes ASTM D6795,which is a standard test method for measuring the effect onfilterability of lubricant compositions after treatment with water anddry ice and a short (30 min) heating time. ASTM D6795 simulates aproblem that may be encountered in a new engine run for a short periodof time, followed by a long period of storage with some water in theoil. ASTM D6795 is designed to determine the tendency of a lubricantcomposition to form a precipitate that can plug an oil filter.

In another embodiment, the lubricant composition passes ASTM D6794,which is a standard test method for measuring the effect onfilterability of lubricant composition after treatment with variousamounts of water and a long (6 h) heating time. ASTM D6794 simulates aproblem that may be encountered in a new engine run for a short periodof time, followed by a long period of storage with some water in theoil. ASTM D6794 is also designed to determine the tendency of thelubricant composition to form a precipitate that can plug an oil filter.

In another embodiment, the lubricant composition passes ASTM D6922,which is a standard test method for determining homogeneity andmiscibility in lubricant compositions. ASTM D6922 is designed todetermine if a lubricant composition is homogeneous and will remain so,and if the lubricant composition is miscible with certain standardreference oils after being submitted to a prescribed cycle oftemperature changes.

In another embodiment, the lubricant composition passes ASTM D5133,which is a standard test method for low temperature, low shear rate,viscosity/temperature dependence of lubricating oils using atemperature-scanning technique. The low-temperature, low-shearviscometric behavior of a lubricant composition determines whether thelubricant composition will flow to a sump inlet screen, then to an oilpump, then to sites in an engine requiring lubrication in sufficientquantity to prevent engine damage immediately or ultimately after coldtemperature starting.

In another embodiment, the lubricant composition passes ASTM D5800and/or ASTM D6417, both of which are test methods for determining anevaporation loss of a lubricant composition. The evaporation loss is ofparticular importance in engine lubrication, because where hightemperatures occur, portions of a lubricant composition can evaporateand thus alter the properties of the lubricant composition.

In another embodiment, the lubricant composition passes ASTM D6557,which is a standard test method for evaluation of rust preventivecharacteristics of lubricant compositions. ASTM D6577 includes a BallRust Test (BRT) procedure for evaluating the anti-rust ability oflubricant compositions. This BRT procedure is particularly suitable forthe evaluation of lubricant compositions under low-temperature andacidic service conditions.

In another embodiment, the lubricant composition passes ASTM D4951 forsulfur content. ASTM D4951 is a standard test method for determinationof additive elements in lubricant compositions by ICP-OES. In addition,the lubricant composition also passes ASTM D2622, which is a standardtest method for sulfur in petroleum products by wavelength dispersivex-ray fluorescence spectrometry.

In another embodiment, the lubricant composition passes ASTM D6891,which is a standard test method for evaluating a lubricant compositionin a sequence IVA spark-ignition engine. ASTM D6891 is designed tosimulate extended engine idling vehicle operation. Specifically, ASTMD6891 measures the ability of a lubricant composition to controlcamshaft lobe wear for spark-ignition engines equipped with an overheadvalve-train and sliding cam followers.

In another embodiment, the lubricant composition passes ASTM D6593,which is a standard test method for evaluating lubricant compositionsfor inhibition of deposit formation in a spark-ignition internalcombustion engine fueled with gasoline and operated underlow-temperature, light-duty conditions. ASTM D6593 is designed toevaluate a lubricant composition's control of engine deposits underoperating conditions deliberately selected to accelerate depositformation.

In another embodiment, the lubricant composition passes ASTM D6709,which is a standard test method for evaluating lubricant compositions ina sequence VIII spark-ignition engine. ASTM D6709 is designed toevaluate lubricant compositions for protection of engines againstbearing weight loss.

In yet another embodiment, the lubricant composition passes ASTMD6984—the standard test method for evaluation of automotive engine oilsin the Sequence IIIF, Spark-Ignition. In other words, the viscosityincrease of the lubricant composition at the end of the test is lessthan 275% relative to the viscosity of the lubricant composition at thebeginning of the test.

In another embodiment, the lubricant composition passes two, three,four, or more of the following standard test methods: ASTM D4951, ASTMD6795, ASTM D6794, ASTM D6922, ASTM D5133, ASTM D6557, ASTM D6891, ASTMD2622, ASTM D6593, and ASTM D6709.

In another embodiment, the lubricant composition passes all of thefollowing standard test methods: ASTM D4951, ASTM D6795, ASTM D6794,ASTM D6922, ASTM D5133, ASTM D6557, ASTM D6891, ASTM D2622, ASTM D6593,and ASTM D6709.

The lubricant composition or the additive package may further include adispersant in addition to the epoxide compound and/or the aminecompound. The dispersant may be a polyalkene amine. The polyalkene amineincludes a polyalkene moiety. The polyalkene moiety is thepolymerization product of identical or different, straight-chain orbranched C₂₋₆ olefin monomers. Examples of suitable olefin monomers areethylene, propylene, 1-butene, isobutene, 1-pentene, 2-methyl butene,1-hexene, 2-methylpentene, 3-methylpentene, and 4-methylpentene. Thepolyalkene moiety has a weight average molecular weight of from 200 to10000, 500 to 10000, or 800 to 5000.

In one embodiment, the polyalkene amine is derived from polyisobutenes.Particularly suitable polysiobutenes are known as “highly reactive”polyisobutenes which feature a high content of terminal double bonds.Terminal double bonds are alpha-olefinic double bonds of the type shownin general formula (XVII):

The bonds shown in general formulas (XVII) are known as vinylidenedouble bones. Suitable highly reactive polypolyisobutenes are, forexample, polyisobutenes which have a fraction of vinylidene double bondsof greater than 70, 80, or 85, mole %. Preference is given in particularto polyisobutenes which have uniform polymer frameworks. Uniform polymerframeworks have in particular those polyisobutenes which are composed ofat least 85, 90, or 95, wt. %, of isobutene units. Such highly reactivepolyisobutenes preferably have a number-average molecular weight in theabovementioned range. In addition, the highly reactive polyisobutenesmay have a polydispersity of from 1.05 to 7, or 1.1 to 2.5. The highlyreactive polyisobutenes may have a polydispersity less than 1.9, or lessthan 1.5. Polydispersity refers to the quotients of weight-averagemolecular weight Mw divided by the number-average molecular weight Mn.

The amine dispersant may include moieties derived from succinicanhydride and having hydroxyl and/or amino and/or amido and/or imidogroups. For example, the dispersant may be derived frompolyisobutenylsuccinic anhydride which is obtainable by reactingconventional or highly reactive polyisobutene having a weight averagemolecular weight of from 500 to 5000 with maleic anhydride by a thermalroute or via the chlorinated polyisobutene. For examples, derivativeswith aliphatic polyamines such as ethylenediamine, diethylenetriamine,triethylenetetramine or tetraethylenepentamine may be used.

To prepare the polyalkene amine, the polyalkene component may beaminated in a known manner. An exemplary process proceeds via thepreparation of an oxo intermediate by hydroformylation and subsequentreductive amination in the presence of a suitable nitrogen compound.

The dispersant may be a poly(oxyalkyl) radical or a polyalkylenepolyamine radical of the general formula (XVIII):

R²⁰—NH—(C₁-C₆-alkylene-NH)_(m)—C₁-C₆-alkylene  (XVIII)

where m is an integer of from 1 to 5, R²⁰ is a hydrogen atom or ahydrocarbyl group having from 1 to 6 carbon atoms with C₁-C₆ alkylenerepresenting the corresponding bridged analogs of the alkyl radicals.The dispersant may also be a polyalkylene imine radical composed of from1 to 10 C₁-C₄ alkylene imine groups; or, together with the nitrogen atomto which they are bonded, are an optionally substituted 5- to 7-memberedheterocyclic ring which is optionally substituted by one to three C₁-C₄alkyl radicals and optionally bears one further ring heteroatom such asoxygen or nitrogen.

Examples of suitable alkenyl radicals include mono- or polyunsaturated,preferably mono- or diunsaturated analogs of alkyl radicals has from 2to 18 carbon atoms, in which the double bonds may be in any position inthe hydrocarbon chain.

Examples of C₄-C₁₈ cycloalkyl radical include cyclobutyl, cyclopentyland cyclohexyl, and also the analogs thereof substituted by 1 to 3 C₁-C₄alkyl radicals. The C₁-C₄ alkyl radicals are, for example, selected frommethyl, ethyl, iso- or n-propyl, n-, iso-, sec- or tert-butyl.

Examples of the arylalkyl radical include a C₁-C₁₈ alkyl group and anaryl group which are derived from a monocyclic or bicyclic fused ornonfused 4- to 7-membered, in particular 6 membered, aromatic orheteroaromatic group, such as phenyl, pyridyl, naphthyl and biphenyl.

If additional dispersants other than the dispersant described above areemployed, these dispersants can be of various types. Suitable examplesof dispersants include polybutenylsuccinic amides or -imides,polybutenylphosphonic acid derivatives and basic magnesium, calcium andbarium sulfonates and phenolates, succinate esters and alkylphenolamines (Mannich bases), and combinations thereof.

If employed, the dispersant can be used in various amounts. Thedispersant may be present in the lubricant composition in an amount offrom 0.01 to 15, 0.1 to 12, 0.5 to 10, or 1 to 8, wt. %, based on thetotal weight of the lubricant composition. Alternatively, the dispersantmay be present in amounts of less than 15, less than 12, less than 10,less than 5, or less than 1, wt. %, each based on the total weight ofthe lubricant composition.

In the additive package, the total weight of the dispersant and theepoxide compound is less than 50, less than 45, less than 40, less than35, or less than 30, wt. %, of the additive package based on the totalweight of the additive package.

The lubricant composition or the additive package may further include anantiwear additive, optionally comprising phosphorous. The antiwearadditive may include sulfur- and/or phosphorus- and/orhalogen-containing compounds, e.g., sulfurised olefins and vegetableoils, alkylated triphenyl phosphates, tritolyl phosphate, tricresylphosphate, chlorinated paraffins, alkyl and aryl di- and trisulfides,amine salts of mono- and dialkyl phosphates, amine salts ofmethylphosphonic acid, diethanolaminomethyltolyltriazole,bis(2-ethylhexyl)aminomethyltolyltriazole, derivatives of2,5-dimercapto-1,3,4-thiadiazole, ethyl3-[(diisopropoxyphosphinothioyl)thio]propionate, triphenyl thiophosphate(triphenylphosphorothioate), tris(alkylphenyl)phosphorothioate andmixtures thereof, diphenyl monononylphenyl phosphorothioate,isobutylphenyl diphenyl phosphorothioate, the dodecylamine salt of3-hydroxy-1,3-thiaphosphetane 3-oxide, trithiophosphoric acid5,5,5-tris[isooctyl 2-acetate], derivatives of 2-mercaptobenzothiazolesuch as1-[N,N-bis(2-ethylhexyl)aminomethyl]-2-mercapto-1H-1,3-benzothiazole,ethoxycarbonyl-5-octyldithio carbamate, and/or combinations thereof.

In some embodiments, the antiwear additive may be exemplified by adihydrocarbyl dithiophosphate salt. The dihydrocarbyl dithiophosphatesalt may be represented by the following general formula (XIX):

[R²¹O(R²²O)PS(S)]₂M  (XIX)

where R²¹ and R²² are each hydrocarbyl groups independently having from1 to 30, 1 to 20, 1 to 15, 1 to 10, or 1 to 5, carbon atoms, wherein Mis a metal atom or an ammonium group. For example, R²¹ and R²² may eachindependently be C₁₋₂₀ alkyl groups, C₂₋₂₀ alkenyl groups, C₃₋₂₀cycloalkyl groups, C₁₋₂₀ aralkyl groups or C₃₋₂₀ aryl groups. The groupsdesignated by R²¹ and R²² may be substituted or unsubstituted. Thehydrocarbyl groups designated by R²¹ and R²² groups may have the samemeaning as described above with respect to R in general formula (I). Themetal atom may be selected from the group including aluminum, lead, tin,manganese, cobalt, nickel, or zinc. The ammonium group may be derivedfrom ammonia or a primary, secondary, or tertiary amine. The ammoniumgroup may be of the formula R²³R²⁴R²⁵R²⁶N⁺, wherein R²³, R²⁴, R²⁵, andR²⁶ each independently represents a hydrogen atom or a hydrocarbyl grouphaving from 1 to 150 carbon atoms. In certain embodiments, R²³, R²⁴,R²⁵, and R²⁶ may each independently be hydrocarbyl groups having from 4to 30 carbon atoms. The hydrocarbyl groups designated by R²³, R²⁴, R²⁵,and R²⁶ may have the same meaning and R in general formula (I). In onespecific embodiment, the dihydrocarbyl dithiophosphate salt is zincdialkyl dithiophosphate. The lubricant composition may include mixturesof different dihydrocarbyl dithiophosphate salts.

In certain embodiments, the dihydrocarbyl dithiophosphate salt includesa mixture of primary and secondary alkyl groups for, R²¹ and R²²,wherein the secondary alkyl groups are in a major molar proportion, suchas at least 60, at least 75, or at least 85, mole %, based on the numberof moles of alkyl groups in the dihydrocarbyl dithiophosphate salt.

In some embodiments, the antiwear additive may be ashless. The antiwearadditive may be further defined as a phosphate. In another embodiment,the antiwear additive is further defined as a phosphite. In stillanother embodiment, the antiwear additive is further defined as aphosphorothionate. The antiwear additive may alternatively be furtherdefined as a phosphorodithioate. In one embodiment, the antiwearadditive is further defined as a dithiophosphate. The antiwear additivemay also include an amine such as a secondary or tertiary amine. In oneembodiment, the antiwear additive includes an alkyl and/or dialkylamine. Structures of suitable non-limiting examples of antiwearadditives are set forth immediately below:

The antiwear additive can be present in the lubricant composition in anamount of from 0.1 to 20, 0.5 to 15, 1 to 10, 0.1 to 5, 0.1 to 1, 0.1 to0.5, or 0.1 to 1.5, wt. %, each based on the total weight of thelubricant composition. Alternatively, the antiwear additive may bepresent in amounts of less than 20, less than 10, less than 5, less than1, less than 0.5, or less than 0.1, wt. %, each based on the totalweight of the lubricant composition. The additive package may alsoinclude the antiwear additive comprising phosphorous in an amount offrom 0.1 to 20, 0.5 to 15, 1 to 10, 0.1 to 5, 0.1 to 1, 0.1 to 0.5, or0.1 to 1.5, wt. %, each based on the total weight of the additivepackage.

The additive package may consist of, or consist essentially of, theantiwear additive and the epoxide compound. It is also contemplated thatthe lubricant composition may consist of, or consist essentially of, theepoxide compound and the antiwear additive in addition to one or more ofadditives that do not compromise the functionality or performance of theepoxide compound. Additionally, it is also contemplated that theadditive package may consist of, or consist essentially of, the epoxidecompound, an amine compound, and the antiwear additive, in addition toone or more additives that do not compromise the functionality orperformance of the epoxide compound.

In various embodiments where the lubricant composition consistsessentially or consists of the base oil and the epoxide compound; thebase oil, the epoxide compound, and the amine compound; or the base oil,the epoxide compound, and the antiwear additive, or the base oil, theamine compound, the epoxide compound, and the antiwear additive, thelubricant composition is free of, or includes less than 0.01, 0.001, or0.0001 wt. % of acids, amine curing agents, anhydrides, triazoles, andoxides.

The lubricant composition or the additive package may additionallyinclude one or more additives to improve various chemical and/orphysical properties of the lubricant composition. These additives may bein addition to the epoxide compound, in addition to the combination ofthe epoxide compound and the amine compound, or in combination with theamine compound, the epoxide compound, and the antiwear additive.Specific examples of the one or more additives include antioxidants,metal deactivators (or passivators), rust inhibitors, viscosity indeximprovers, pour point depressors, dispersants, detergents, andantifriction additives. Each of the additives may be used alone or incombination. The one or more additives can be used in various amounts,if employed. The lubricant composition may be formulated with theaddition of several auxiliary components to achieve certain performanceobjectives for use in certain applications. For example, the lubricantcomposition may be a rust and oxidation lubricant formulation, ahydraulic lubricant formulation, turbine lubricant oil, and an internalcombustion engine lubricant formulation. Accordingly, it is contemplatedthat the base oil may be formulated to achieve these objectives asdiscussed below.

If employed, the antioxidant can be of various types. Suitableantioxidants include alkylated monophenols, for example2,6-di-tert-butyl-4-methylphenol, 2-tert-butyl-4,6-dimethylphenol,2,6-di-tert-butyl-4-ethylphenol, 2,6-di-tert-butyl-4-n-butylphenol,2,6-di-tert-butyl-4-isobutylphenol, 2,6-dicyclopentyl-4-methylphenol,2-(α-methylcyclohexyl)-4,6-dimethylphenol,2,6-dioctadecyl-4-methylphenol, 2,4,6-tricyclohexylphenol,2,6-di-tert-butyl-4-methoxymethylphenol, 2,6-di-nonyl-4-methylphenol,2,4-dimethyl-6(1′-methylundec-1′-yl)phenol,2,4-dimethyl-6-(1′-methylheptadec-1′-yl)phenol,2,4-dimethyl-6-(1′-methyltridec-1′-yl)phenol, and combinations thereof.

Further examples of suitable antioxidants includesalkylthiomethylphenols, for example2,4-dioctylthiomethyl-6-tert-butylphenol,2,4-dioctylthiomethyl-6-methylphenol,2,4-dioctylthiomethyl-6-ethylphenol,2,6-didodecylthiomethyl-4-nonylphenol, and combinations thereof.Hydroquinones and alkylated hydroquinones, for example2,6-di-tert-butyl-4-methoxyphenol, 2,5-di-tert-butylhydroquinone,2,5-di-tert-amylhydroquinone, 2,6-diphenyl-4-octadecyloxyphenol,2,6-di-tert-butylhydroquinone, 2,5-di-tert-butyl-4-hydroxyanisole,3,5-di-tert-butyl-4-hydroxyanisole, 3,5-di-tert-butyl-4-hydroxyphenylstearate, bis-(3,5-di-tert-butyl-4-hydroxyphenyl)adipate, andcombinations thereof, may also be utilized.

Furthermore, hydroxylated thiodiphenyl ethers, for example2,2′-thiobis(6-tert-butyl-4-methylphenol), 2,2′-thiobis(4-octylphenol),4,4′-thiobis(6-tert-butyl-3-methylphenol),4,4′-thiobis(6-tert-butyl-2-methylphenol),4,4′-thiobis-(3,6-di-sec-amylphenol),4,4′-bis-(2,6-dimethyl-4-hydroxyphenyl)disulfide, and combinationsthereof, may also be used.

It is also contemplated that alkylidenebisphenols, for example2,2′-methylenebis(6-tert-butyl-4-methylphenol),2,2′-methylenebis(6-tert-butyl-4-ethylphenol),2,2′-methylenebis[4-methyl-6-(α-methylcyclohexyl)phenol],2,2′-methylenebis(4-methyl-6-cyclohexylphenol),2,2′-methylenebis(6-nonyl-4-methylphenol),2,2′-methylenebis(4,6-di-tert-butylphenol),2,2′-ethylidenebis(4,6-di-tert-butylphenol),2,2′-ethylidenebis(6-tert-butyl-4-isobutylphenol),2,2′-methylenebis[6-(α-methylbenzyl)-4-nonylphenol],2,2′-methylenebis[6-(α,α-dimethylbenzyl)-4-nonylphenol],4,4′-methylenebis(2,6-di-tert-butylphenol),4,4′-methylenebis(6-tert-butyl-2-methylphenol),1,1-bis(5-tert-butyl-4-hydroxy-2-methylphenyl)butane,2,6-bis(3-tert-butyl-5-methyl-2-hydroxybenzyl)-4-methylphenol,1,1,3-tris(5-tert-butyl-4-hydroxy-2-methylphenyl)butane,1,1-bis(5-tert-butyl-4-hydroxy-2-methyl-phenyl)-3-n-dodecylmercaptobutane, ethylene glycolbis[3,3-bis(3′-tert-butyl-4′-hydroxyphenyl)butyrate],bis(3-tert-butyl-4-hydroxy-5-methyl-phenyl)dicyclopentadiene,bis[2-(3′-tert-butyl-2′-hydroxy-5′-methylbenzyl)-6-tert-butyl-4-methylphenyl]terephthalate,1,1-bis-(3,5-dimethyl-2-hydroxyphenyl)butane,2,2-bis-(3,5-di-tert-butyl-4-hydroxyphenyl)propane,2,2-bis-(5-tert-butyl-4-hydroxy-2-methylphenyl)-4-n-dodecylmercaptobutane,1,1,5,5-tetra-(5-tert-butyl-4-hydroxy-2-methyl phenyl)pentane, andcombinations thereof may be utilized as antioxidants in the lubricantcomposition.

O-, N- and S-benzyl compounds, for example3,5,3′,5′-tetra-tert-butyl-4,4′-dihydroxydibenzyl ether,octadecyl-4-hydroxy-3,5-dimethylbenzylmercaptoacetate,tris-(3,5-di-tert-butyl-4-hydroxybenzyl)amine,bis(4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl)dithiol terephthalate,bis(3,5-di-tert-butyl-4-hydroxybenzyl)sulfide,isooctyl-3,5di-tert-butyl-4-hydroxy benzylmercaptoacetate, andcombinations thereof, may also be utilized.

Hydroxybenzylated malonates, for exampledioctadecyl-2,2-bis-(3,5-di-tert-butyl-2-hydroxybenzyl)-malonate,di-octadecyl-2-(3-tert-butyl-4-hydroxy-5-methylbenzyl)-malonate,di-dodecylmercaptoethyl-2,2-bis-(3,5-di-tert-butyl-4-hydroxybenzyl)malonate,bis[4-(1,1,3,3-tetramethylbutyl)phenyl]-2,2-bis(3,5-di-tert-butyl-4-hydroxybenzyl)malonate,and combinations thereof are also suitable for use as antioxidants.

Triazine compounds, for example2,4-bis(octylmercapto)-6-(3,5-di-tert-butyl-4-hydroxyanilino)-1,3,5-triazine,2-octylmercapto-4,6-bis(3,5-di-tert-butyl-4-hydroxyanilino)-1,3,5-triazine,2-octylmercapto-4,6-bis(3,5-di-tert-butyl-4-hydroxyphenoxy)-1,3,5-triazine,2,4,6-tris(3,5-di-tert-butyl-4-hydroxyphenoxy)-1,2,3-triazine,1,3,5-tris(3,5-di-tert-butyl-4-hydroxybenzyl)isocyanurate,1,3,5-tris(4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl2,4,6-tris(3,5-di-tert-butyl-4-hydroxyphenylethyl)-1,3,5-triazine,1,3,5-tris(3,5-di-tert-butyl-4-hydroxyphenylpropionyl)-hexahydro-1,3,5-triazine,1,3,5-tris-(3,5-dicyclohexyl-4-hydroxybenzyl)-isocyanurate, andcombinations thereof, may also be used.

Additional examples of antioxidants include aromatic hydroxybenzylcompounds, for example,1,3,5-tris-(3,5-di-tert-butyl-4-hydroxybenzyl)-2,4,6-trimethylbenzene,1,4-bis(3,5-di-tert-butyl-4-hydroxybenzyl)-2,3,5,6-tetramethylbenzene,2,4,6-tris(3,5-di-tert-butyl-4-hydroxybenzyl)phenol, and combinationsthereof. Benzylphosphonates, for exampledimethyl-2,5-di-tert-butyl-4-hydroxybenzylphosphonate,diethyl-3,5-di-tert-butyl-4-hydroxybenzylphosphonate,dioctadecyl3,5-di-tert-butyl-4-hydroxybenzylphosphonate,dioctadecyl-5-tert-butyl-4-hydroxy-3-methylbenzylphosphonate, thecalcium salt of the monoethyl ester of3,5-di-tert-butyl-4-hydroxybenzylphosphonic acid, and combinationsthereof, may also be utilized. In addition, acylaminophenols, forexample 4-hydroxylauranilide, 4-hydroxystearanilide, and octylN-(3,5-di-tert-butyl-4-hydroxyphenyl)carbamate.

Esters of [3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionic acid withmono- or polyhydric alcohols, e.g. with methanol, ethanol, octadecanol,1,6-hexanediol, 1,9-nonanediol, ethylene glycol, 1,2-propanediol,neopentyl glycol, thiodiethylene glycol, diethylene glycol, triethyleneglycol, pentaerythritol, tris(hydroxyethyl)isocyanurate,N,N′-bis(hydroxyethyl)oxamide, 3-thiaundecanol, 3-thiapentadecanol,trimethylhexanediol, trimethylolpropane,4-hydroxymethyl-1-phospha-2,6,7-trioxabicyclo[2.2.2]octane, andcombinations thereof, may also be used. It is further contemplated thatesters of β-(5-tert-butyl-4-hydroxy-3-methylphenyl)-propionic acid withmono- or polyhydric alcohols, e.g. with methanol, ethanol, octadecanol,1,6-hexanediol, 1,9-nonanediol, ethylene glycol, 1,2-propanediol,neopentyl glycol, thiodiethylene glycol, diethylene glycol, triethyleneglycol, pentaerythritol, tris(hydroxyethyl)isocyanurate,N,N′-bis(hydroxyethyl)oxamide, 3-thiaundecanol, 3-thiapentadecanol,trimethylhexanediol, trimethylolpropane,4-hydroxymethyl-1-phospha-2,6,7-trioxabicyclo[2.2.2]octane, andcombinations thereof, may be used.

Additional examples of suitable antioxidants include those that includenitrogen, such as amides ofβ-(3,5-di-tert-butyl-4-hydroxyphenyl)propionic acid, e.g.,N,N-bis(3,5-di-tert-butyl-4-hydroxyphenylpropionyl)hexamethylenediamine,N,N′-bis(3,5-di-tert-butyl-4-hydroxyphenyl-propionyl)trimethylenediamine,N,N′-bis(3,5-di-tert-butyl-4-hydroxyphenylpropionyl)hydrazine. Othersuitable examples of antioxidants include aminic antioxidants such asN,N′-diisopropyl-p-phenylenediamine,N,N′-di-sec-butyl-p-phenylenediamine,N,N′-bis(1,4-dimethylpentyl)-p-phenylenediamine,N,N′-bis(1-ethyl-3-methylpentyl)-p-phenylenediamine,N,N′-bis(1-methylheptyl)-p-phenylenediamine,N,N′-dicyclohexyl-p-phenylenediamine, N,N′-diphenyl-p-phenylenediamine,N,N′-bis(2-naphthyl)-p-phenylenediamine,N-isopropyl-N′-phenyl-p-phenylenediamine,N-(1,3-dimethyl-butyl)-N′-phenyl-p-phenylenediamine,N-(1-methylheptyl)-N′-phenyl-p-phenylenediamine,N-cyclohexyl-N′-phenyl-p-phenylenediamine,4-(p-toluenesulfamoyl)diphenylamine,N,N′-dimethyl-N,N′-di-sec-butyl-p-phenylenediamine, diphenylamine,N-allyldiphenylamine, 4-isopropoxydiphenylamine,N-phenyl-1-naphthylamine, N-phenyl-2-naphthylamine, octylateddiphenylamine, for example p,p′-di-tert-octyldiphenylamine,4-n-butylaminophenol, 4-butyrylaminophenol, 4-nonanoylaminophenol,4-dodecanoylaminophenol, 4-octadecanoylaminophenol,bis(4-methoxyphenyl)amine, 2,6-di-tert-butyl-4-dimethylaminomethylphenol, 2,4′-diaminodiphenylmethane, 4,4′-diaminodiphenylmethane,N,N,N′,N′-tetramethyl-4,4′-diaminodiphenylmethane,1,2-bis[(2-methyl-phenyl)amino]ethane, 1,2-bis(phenylamino)propane,(o-tolyl)biguanide, bis[4-(1′,3′-dimethylbutyl)phenyl]amine,tert-octylated N-phenyl-1-naphthylamine, a mixture of mono- anddialkylated tert-butyl/tert-octyldiphenylamines, a mixture of mono- anddialkylated isopropyl/isohexyldiphenylamines, mixtures of mono- anddialkylated tert-butyldiphenylamines,2,3-dihydro-3,3-dimethyl-4H-1,4-benzothiazine, phenothiazine,N-allylphenothiazine, N,N,N′,N′-tetraphenyl-1,4-diaminobut-2-ene, andcombinations thereof.

Even further examples of suitable antioxidants include aliphatic oraromatic phosphites, esters of thiodipropionic acid or of thiodiaceticacid, or salts of dithiocarbamic or dithiophosphoric acid,2,2,12,12-tetramethyl-5,9-dihydroxy-3,7,1-trithiamidecane and2,2,15,15-tetramethyl-5,12-dihydroxy-3,7,10,14-tetrathiahexadecane, andcombinations thereof. Furthermore, sulfurized fatty esters, sulfurizedfats and sulfurized olefins, and combinations thereof, may be used.

If employed, the antioxidant can be used in various amounts. Theantioxidant may be present in the lubricant composition in an amount offrom 0.01 to 5, 0.1 to 3, or 0.5 to 2, wt. %, based on the total weightof the lubricant composition. Alternatively, the antioxidant may bepresent in amounts of less than 5, less than 3, or less than 2, wt. %,based on the total weight of the lubricant composition.

If employed, the metal deactivator can be of various types. Suitablemetal deactivators include benzotriazoles and derivatives thereof, forexample 4- or 5 alkylbenzotriazoles (e.g. tolutriazole) and derivativesthereof, 4,5,6,7-tetrahydrobenzotriazole and5,5′-methylenebisbenzotriazole; Mannich bases of benzotriazole ortolutriazole, e.g. 1-[bis(2-ethylhexyl)aminomethyl)tolutriazole and1-[bis(2-ethylhexyl)aminomethyl)benzotriazole; andalkoxyalkylbenzotriazoles such as 1-(nonyloxymethyl)benzotriazole,1-(1-butoxyethyl)benzotriazole and 1-(1-cyclohexyloxybutyl)tolutriazole,and combinations thereof.

Additional examples of suitable metal deactivators include1,2,4-triazoles and derivatives thereof, and Mannich bases of1,2,4-triazoles, such as 1-[bis(2-ethylhexyl)aminomethyl-1,2,4-triazole;alkoxyalkyl-1,2,4-triazoles such as 1-(1-butoxyethyl)-1,2,4-triazole;and acylated 3-amino-1,2,4-triazoles, imidazole derivatives, for example4,4′-methylenebis(2-undecyl-5-methylimidazole) andbis[(N-methyl)imidazol-2-yl]carbinol octyl ether, and combinationsthereof. Further examples of suitable metal deactivators includesulfur-containing heterocyclic compounds, for example2-mercaptobenzothiazole, 2,5-dimercapto-1,3,4-thiadiazole andderivatives thereof; and3,5-bis[di(2-ethylhexyl)aminomethyl]-1,3,4-thiadiazolin-2-one, andcombinations thereof. Even further examples of metal deactivatorsinclude amino compounds, for example salicylidenepropylenediamine,salicylaminoguanidine and salts thereof, and combinations thereof.

If employed, the metal deactivator can be used in various amounts. Themetal deactivator may be present in the lubricant composition in anamount of from 0.01 to 0.1, 0.05 to 0.01, or 0.07 to 0.1, wt. %, basedon the total weight of the lubricant composition. Alternatively, themetal deactivator may be present in amounts of less than 1.0, less than0.7, or less than 0.5, wt. %, based on the total weight of the lubricantcomposition.

If employed, the rust inhibitor and/or friction modifier can be ofvarious types. Suitable examples of rust inhibitors and/or frictionmodifiers include organic acids, their esters, metal salts, for examplealkyl- and alkenylsuccinic acids and their partial esters with alcohols,diols or hydroxycarboxylic acids, partial amides of alkyl- andalkenylsuccinic acids, 4-nonylphenoxyacetic acid, alkoxy- andalkoxyethoxycarboxylic acids such as dodecyloxyacetic acid,dodecyloxy(ethoxy)acetic acid, and also N-oleoylsarcosine, sorbitanmonooleate, lead naphthenate, alkenylsuccinic anhydrides, for example,dodecenylsuccinic anhydride, 2-carboxymethyl-1-dodecyl-3-methylglycerol,and combinations thereof. Further examples include heterocycliccompounds, for example: substituted imidazolines and oxazolines, and2-heptadecenyl-1-(2-hydroxyethyl)imidazoline, phosphorus-containingcompounds, for example: amine salts of phosphoric acid partial esters orphosphonic acid partial esters, molybdenum-containing compounds, such asmolydbenum dithiocarbamate and other sulphur and phosphorus containingderivatives, sulfur-containing compounds, for example: bariumdinonylnaphthalenesulfonates, calcium petroleum sulfonates,alkylthio-substituted aliphatic carboxylic acids, esters of aliphatic2-sulfocarboxylic acids and salts thereof, glycerol derivatives, forexample: glycerol monooleate,1-(alkylphenoxy)-3-(2-hydroxyethyl)glycerols,1-(alkylphenoxy)-3-(2,3-dihydroxypropyl) glycerols and2-carboxyalkyl-1,3-dialkylglycerols, and combinations thereof.

If employed, the rust inhibitor and/or friction modifier can be used invarious amounts. The rust inhibitor and/or friction modifier may bepresent in the lubricant composition in an amount of from 0.01 to 0.1,0.05 to 0.01, or 0.07 to 0.1, wt. %, based on the total weight of thelubricant composition. Alternatively, the rust inhibitor and/or frictionmodifier may be present in amounts of less than 1, less than 0.7, orless than 0.5, wt. %, based on the total weight of the lubricantcomposition.

If employed, the viscosity index improver can be of various types.Suitable examples of viscosity index improvers include polyacrylates,polymethacrylates, vinylpyrrolidone/methacrylate copolymers,polyvinylpyrrolidones, polybutenes, olefin copolymers, styrene/acrylatecopolymers and polyethers, and combinations thereof.

If employed, the viscosity index improver can be used in variousamounts. The viscosity index improver may be present in the lubricantcomposition in an amount of from 0.01 to 20, 1 to 15, or 1 to 10, wt. %,based on the total weight of the lubricant composition. Alternatively,the viscosity index improver may be present in amounts of less than 10,less than 8, or less than 5, wt. %, based on the total weight of thelubricant composition.

If employed, the pour point depressant can be of various types. Suitableexamples of pour point depressants include polymethacrylate andalkylated naphthalene derivatives, and combinations thereof.

If employed, the pour point depressant can be used in various amounts.The pour point depressant may be present in the lubricant composition inan amount of from 0.01 to 0.1, 0.05 to 0.01, or 0.07 to 0.1, wt. %, eachbased on the total weight of the lubricant composition. Alternatively,the pour point depressant may be present in amounts of less than 1.0,less than 0.7, or less than 0.5, wt. %, based on the total weight of thelubricant composition.

If employed, the detergent can be of various types. Suitable examples ofdetergents include overbased or neutral metal sulphonates, phenates andsalicylates, and combinations thereof.

If employed, the detergent can be used in various amounts. The detergentmay be present in the lubricant composition in an amount of from 0.01 to5, 0.1 to 4, 0.5 to 3, or 1 to 3, wt. %, based on the total weight ofthe lubricant composition. Alternatively, the detergent may be presentin amounts of less than 5, less than 4, less than 3, less than 2, orless than 1, wt. %, based on the total weight of the lubricantcomposition.

Preferred lubricant compositions provided for use and used pursuant tothis invention include those which pass the CEC L-39-T96 sealcompatibility test. The CEC L-39-T96 test involves keeping a testspecimen of a fluoropolymer in a lubricant composition at 150° C. Theseal specimens are then removed and dried and the properties of the sealspecimens are assessed and compared to the seal specimens which were notheated in the lubricant composition. The percent change in theseproperties is assessed to quantify the compatibility of thefluoropolymer seal with the lubricant composition. The incorporation ofthe epoxide compound into the lubricant composition decreases thetendency of the lubricant composition to degrade the seals versuslubricant compositions which are free from the epoxide compound.

The pass/fail criteria include maximum variation of certaincharacteristics after immersion for 7 days in fresh oil withoutpre-aging. The maximum variation for each characteristic depends on thetype of elastomer used, the type of engine used, and whether anaftertreatment device is utilized.

The characteristics measured before and after immersion includedHardness DIDC (points); Tensile Strength (%); Elongation at Rupture (%);Volume Variation (%). For heavy-duty diesel engines, the pass/failcriteria are presented below in Table 1:

TABLE 1 Fluoropolymer Seal Compatibility for CEC L-39-T96 Heavy-DutyDiesel Engines Elastomer Type Property RE1 Hardness DIDC, points −1/+5Tensile Strength, % −50/+10 Elongation at Rupture, % −60/+10 VolumeVariation, % −1/+5

In these tests, a conventional lubricant composition passes the test ifthe exposed test specimen exhibits a change in hardness from −1% to +5%;a tensile strength (as compared to an untested specimen) from −50% to+10%; a change in elongation at rupture (as compared to an untestedspecimen) from −60% to +10%; and a volume variation (as compared to anuntested specimen) from −1% to +5%.

When the lubricant composition is tested according to CEC L-39-T96 forHeavy-Duty Diesel Engines, the change in hardness can range from −1 to5%, −0.5 to 5%, −0.1 to 5%, 0.5 to 5%, or 1 to 5%; the change in tensilestrength can range from −50 to 10%, −45 to 10%, −40 to 10%, or −35 to10%; the change in elongation at rupture can range from −60 to 10%, −55to 10%, −50 to 10%, or −45 to 10%; and the change in volume variationcan range from −1 to 5%, −0.75 to 5%, −0.5 to 5%, −0.1 to 5%, or 0 to5%.

When the epoxide composition is used in the lubricant compositionsdescribed, the resulting lubricant composition has a fluoropolymercompatibility such that a fluoropolymer seal submerged in said lubricantcomposition exhibits a change in tensile strength of less than 10, lessthan 15, less than 20, less than 25, less than 30, less than 35, lessthan 40, less than 45, less than 50, less than 55, or less than 60, %,when tested according to CEC L-39-T96 for Heavy-Duty Diesel Engines.Similarly, when the epoxide compound is used in the lubricantcompositions described, the resulting lubricant composition has afluoropolymer compatibility such that a fluoropolymer exhibits a changein elongation at rupture of less than 20, less than 25, less than 30,less than 35, less than 40, less than 45, less than 50, less than 55, orless than 60, %, when tested according to CEC L-39-T96 for Heavy-DutyDiesel Engines.

Some of the compounds described above may interact in the lubricantcomposition, so that the components of the lubricant composition infinal form may be different from those components that are initiallyadded or combined together. Some products formed thereby, includingproducts formed upon employing the lubricant composition of thisinvention in its intended use, are not easily described or describable.Nevertheless, all such modifications, reaction products, and productsformed upon employing the lubricant composition of this invention in itsintended use, are expressly contemplated and hereby included herein.Various embodiments of this invention include one or more of themodification, reaction products, and products formed from employing thelubricant composition, as described above.

A method of lubricating a system is provided. The method includescontacting the system with the lubricant composition described above.The system may further include an internal combustion engine.Alternatively, the system may further include any combustion engine orapplication that utilizes a lubricant composition. The system includesat least one fluoropolymer seal.

The method may include providing the lubricant composition to thecrankcase of the internal combustion engine, providing a fuel in acombustion chamber of the internal combustion engine, and combusting thefuel in an internal combustion engine.

The fluoropolymer seal may include a fluoroelastomer. Thefluoroelastomer may be categorized under ASTM D1418 and ISO 1629designation of FKM for example. The fluoroelastomer may includecopolymers of hexafluoropropylene (HFP) and vinylidene fluoride (VDF ofVF2), terpolymers of tetrafluoroethylene (TFE), vinylidene fluoride andhexafluoropropylene, perfluoromethylvinylether (PMVE), copolymers of TFEand propylene and copolymers of TFE, PMVE and ethylene. The fluorinecontent varies for example between 66 to 70 wt. %, based on the totalweight of the fluoropolymer seal. FKM is fluoro-rubber of thepolymethylene type having substituent fluoro and perfluoroalkyl orperfluoroalkoxy groups on the polymer chain.

In addition, a method of forming the lubricant composition is provided.The method includes combining the base oil and the epoxide compound,and, optionally, the amine compound and/or the antiwear additive. Theepoxide compound may be incorporated into the base oil in any convenientway. Thus, the epoxide compound can be added directly to the base oil bydispersing or dissolving it in the base oil at the desired level ofconcentration. Alternatively, the base oil may be added directly to theepoxide compound in conjunction with agitation until the epoxidecompound is provided at the desired level of concentration. Suchblending may occur at ambient or lower temperatures, such as 30, 25, 20,15, 10, or 5° C.

Examples

Without being limited, in the below examples, exemplary lubricantcompositions were formulated by blending each of the components togetheruntil homogeneity was achieved. A partially formulated lubricantcomposition containing dispersant, detergent, aminic antioxidant,phenolic antioxidant, anti-foam, base oil, pour point depressant andviscosity modifier was prepared. This lubricant composition, which isrepresentative of a commercial crankcase lubricant, is designated as the“reference lubricant” and used as a baseline to demonstrate the effectsof the epoxide compound on TBN and seal compatibility.

The reference lubricant was combined with various different epoxidecompounds to demonstrate the effect of the epoxide compound on TBN andseal compatibility. Other components were combined with the referencelubricant in combination with the epoxide compound to demonstratesynergies between the epoxide compound and these other components withrespect to TBN and seal compatibility.

The epoxide compound used in examples 5-10, 15, and 31-34 is3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexane carboxylate. The epoxidecompound used in example 16 is 1,4-butanediol diglycidyl ether. Theepoxide compound used in example 17 is 1,2,7,8-diepoxyoctane. Theepoxide compound used in examples 18 and 22 is glycidol. The epoxidecompound used in examples 19 and 23 isN-tert-butyl-2,3-epoxypropionamide. The epoxide compound used inexamples 20 and 24 is N-isopropyl-2,3-epoxypropionamide. The epoxidecompound used in examples 21 and 25 is n-butyl-2,3-epoxy propionate.

The amine compound used in examples 8, 9, 11, 22-25, 27, and 31 is(2,2,6,6-tetramethyl-4-piperidyl)dodecanoate. The amine compound used inexamples 12, 28, and 32 is(1,2,2,6,6-pentamethyl-4-piperidyl)dodecanoate. The amine compound usedin examples 13, 29, and 33 is 1-dodecylamine. The amine compound used inexamples 14, 30, and 34 is Infineum C9232 (a 950 MW PIPSA-PAMdispersant).

The antiwear additive used in examples 2, 5, and 8 is Infineum C9417 (amixed primary/secondary dihydrocarbyldithiophosphate salt. The antiwearadditive used in examples 3, 6, and 15-34 is HiTEC 7169 (a secondarydithiodihydrocarbylphosphate salt). The antiwear additive used inexamples 4, 7, and 9 is ELCO 108 (a primarydithiodihydrocarbyldiphosphate salt).

The respective amount of the reference lubricant and any additionalcomponents for each of the examples are shown in Tables 2-7 below:

TABLE 2 Formulations of Examples #1-#7 Example # 1 2 3 4 5 6 7 ReferenceLubricant (g) 80 80 80 80 80 80 80 Additional Base Oil (g) 20 18.8718.87 18.87 18.37 18.37 18.37 Epoxide Compound (g) 0 0 0 0 0.50 0.500.50 Practical Amine Compound (g) 0 0 0 0 0 0 0 Antiwear Additive (g) 01.13 1.13 1.13 1.13 1.13 1.13 Total Weight (g) 100 100 100 100 100 100100

TABLE 3 Formulations of Examples #8-#14 Example # 8 9 10 11 12 13 14Reference Lubricant (g) 80 80 80 80 80 80 80 Additional Base Oil (g)17.17 17.17 19.5 18.8 18.72 19.32 14.29 Epoxide Compound (g) 0.50 0.500.50 0 0 0 0 Amine Compound (g) 1.20 1.20 0 1.20 1.29 0.68 5.71 AntiwearAdditive (g) 1.13 1.13 0 0 0 0 0 Total Weight (g) 100 100 100 100 100100 100

TABLE 4 Formulations of Examples #15-#21 Example # 15 16 17 18 19 20 21Reference Lubricant (g) 80 80 80 80 80 80 80 Additional Base Oil (g)18.37 18.47 18.59 18.58 18.30 18.36 18.30 Epoxide Compound (g) 0.50 0.400.28 0.29 0.57 0.51 0.57 Amine Compound (g) 0 0 0 0 0 0 0 AntiwearAdditive (g) 1.13 1.13 1.13 1.13 1.13 1.13 1.13 Total Weight (g) 100 100100 100 100 100 100

TABLE 5 Formulations of Examples #22-25 Example # 22 23 24 25 ReferenceLubricant (g) 80 80 80 80 Additional Base Oil (g) 17.38 17.10 17.1617.10 Epoxide Compound (g) 0.29 0.57 0.51 0.57 Amine Compound (g) 1.201.20 1.2 1.20 Antiwear Additive (g) 1.13 1.13 1.13 1.13 Total Weight (g)100 100 100 100

TABLE 6 Formulations of Examples #26-#30 Example # 26 27 28 29 30Reference Lubricant (g) 80 80 80 80 80 Additional Base Oil (g) 18.8717.67 17.59 18.19 13.16 Epoxide Compound (g) 0 0 0 0 0 Amine Compound(g) 0 1.2 1.29 0.68 5.71 Antiwear Additive (g) 1.13 1.13 1.13 1.13 1.13Total Weight (g) 100 100 100 100 100

TABLE 7 Formulations of Examples #31-#34 Example # 31 32 33 34 ReferenceLubricant (g) 80 80 80 80 Additional Base Oil (g) 17.17 17.09 17.6912.66 Epoxide Compound (g) 0.50 0.50 0.50 0.50 Amine Compound (g) 1.201.29 0.68 5.71 Antiwear Additive (g) 1.13 1.13 1.13 1.13 Total Weight(g) 100 100 100 100

The TBN of the exemplary lubricant compositions were tested according toASTM D2896 and ASTM D4739. These test methods can be used to indicaterelative changes that occur in the lubricant composition during useunder oxidizing or other service conditions regardless of the color orother properties of the resulting lubricant composition.

The seal compatibility of the exemplary lubricant compositions weretested according to the industry-standard CEC L-39-T96 sealcompatibility test. The CEC-L-39-T96 seal compatibility test isperformed by submitting the seal or gaskets in the lubricantcomposition, heating the lubricant composition with the seal containedtherein to an elevated temperature, and maintaining the elevatedtemperature for a period of time. The seals are then removed and dried,and the mechanical properties of the seal are assessed and compared tothe seal specimens which were not heated in the lubricant composition.The percent change in these properties is analyzed to assess thecompatibility of the seal with the lubricant composition.

The results of the TBN and seal compatibility tests are shown below inTables 8-13:

TABLE 8 TBN and Seal Compatibility Test Results - Examples #1-#7 Example# 1 2 3 4 5 6 7 Volume Change (%) 0.4 0.6 0.4 0.4 0.5 0.5 0.5 PointsHardness DIDC 3 0 1 1 1 1 1 Tensile Strength (%) −23 −9 −6 −6 −7 −12 −8Elongation at Rupture (%) −47 −40 −27 −24 −22 −27 −23 TBN by ASTM D4739(mg 9.16 9.05 9.01 9.42 9.80 9.37 9.43 KOH/g) TBN by ASTM D 2896 (mg12.18 12.12 12.04 12.23 13.80 13.56 14.38 KOH/g)

TABLE 9 TBN and Seal Compatibility Test Results - Examples #8-#14Example # 8 9 10 11 12 13 14 Volume Change (%) 0.9 1 1.5 0.7 0.7 21 0.3Points Hardness DIDC 3 2 2 4 4 12 4 Tensile Strength (%) −23 −17 −7 −24−23 −66 −28 Elongation at Rupture (%) −42 −33 −45 −50 −49 −72 −49 TBN byASTM D4739 11.28 11.53 9.02 10.94 10.99 11.21 10.94 (mg KOH/g) TBN byASTM D 2896 15.34 16.42 14.00 13.14 13.12 13.91 14.76 (mg KOH/g)

TABLE 10 TBN and Seal Compatibility Test Results - Examples #15-#21Example # 15 16 17 18 19 20 21 Volume 0.5 0.6 0.6 0.4 0.6 0.8 0.5 Change(%) Points 0 −1 −1 0 1 2 0 Hardness DIDC Tensile 5 2 3 2 −4 −12 8Strength (%) Elongation at −19 −20 −4 −9 −23 −30 −4 Rupture (%) TBN byASTM 9.37 9.18 9.12 9.49 9.22 9.45 9.12 D4739 (mg KOH/g) TBN by ASTM12.97 12.14 12.51 12.96 12.51 12.48 12.59 D 2896 (mg KOH/g)

TABLE 11 TBN and Seal Compatibility Test Results - Examples #22-#25Example # 22 23 24 25 Volume Change (%) 0.7 0.9 0.9 0.8 Points HardnessDIDC 0 2 3 1 Tensile Strength (%) −9 −24 −32 −13 Elongation at Rupture(%) −18 −46 −54 −32 TBN by ASTM D4739 11.66 11.21 10.99 11.42 (mg KOH/g)TBN by ASTM D 2896 14.67 14.66 14.75 14.55 (mg KOH/g)

TABLE 12 TBN and Seal Compatibility Test Results - Examples #26-#30Example # 26 27 28 29 30 Volume Change (%) 0.4 0.9 1 5.7 0.6 PointsHardness DIDC 0 3 3 14 4 Tensile Strength (%) −3 −13 −14 −67 −27Elongation at Rupture −21 −52 −55 −78 −53 (%) TBN by ASTM D4739 8.639.81 10.36 10.24 10.40 (mg KOH/g) TBN by ASTM D 2896 11.64 13.15 13.3813.04 14.55 (mg KOH/g)

TABLE 13 TBN and Seal Compatibility Test Results - Examples #31-#34Example # 31 32 33 34 Volume Change (%) 0.8 0.7 8.1 0.6 Points HardnessDIDC 0 0 12 3 Tensile Strength (%) −6 −3 −66 −26 Elongation at Rupture(%) −23 −19 −75 −53 TBN by ASTM D4739 10.84 10.93 10.85 11.08 (mg KOH/g)TBN by ASTM D 2896 14.98 15.15 15.02 16.45 (mg KOH/g)

These examples demonstrate that the epoxide compound improves the TBNand seal compatibility of a lubricant composition. For example, theexamples demonstrate that lubricant compositions that include theepoxide compound demonstrate improved TBN, according to ASTM D4739and/or ASTM D2896, even when combined with components that would notordinarily be expected to affect, or significantly affect, the TBN ofthe lubricant composition. Furthermore, the examples demonstrate thatlubricant compositions which include the epoxide compound demonstrateimproved seal compatibility in terms of in terms of volume change,points hardness, tensile strength and/or elongation at rupture, evenwhen combined with components that would ordinary be expected tonegatively affect the seal compatibility of the lubricant composition ina significant way. In summary, lubricant compositions that include theepoxide compound demonstrate superior results when compared to lubricantcompositions that do not include the epoxide compound.

It is to be understood that the appended claims are not limited toexpress and particular compounds, compositions, or methods described inthe detailed description, which may vary between particular embodimentsthat fall within the scope of the appended claims. With respect to anyMarkush groups relied upon herein for describing particular features oraspects of various embodiments, it is to be appreciated that different,special, and/or unexpected results may be obtained from each member ofthe respective Markush group independent from all other Markush members.Each member of a Markush group may be relied upon individually and/or incombination and provides adequate support for specific embodimentswithin the scope of the appended claims.

It is also to be understood that any ranges and subranges relied upon indescribing various embodiments of the present invention independentlyand collectively fall within the scope of the appended claims and areunderstood to describe and contemplate all ranges, including wholeand/or fractional values therein, even if such values are not expresslywritten herein. One of skill in the art readily recognizes that theenumerated ranges and subranges sufficiently describe and enable variousembodiments of the present invention and such ranges and subranges maybe further delineated into relevant halves, thirds, quarters, fifths,and so on. As just one example, a range “of from 0.1 to 0.9” may befurther delineated into a lower third, i.e., from 0.1 to 0.3, a middlethird, i.e., from 0.4 to 0.6, and an upper third, i.e., from 0.7 to 0.9,which individually and collectively are within the scope of the appendedclaims and may be relied upon individually and/or collectively andprovide adequate support for specific embodiments within the scope ofthe appended claims.

In addition, with respect to the language which defines or modifies arange, such as “at least,” “greater than,” “less than,” “no more than,”and the like, it is to be understood that such language includessubranges and/or an upper or lower limit. As another example, a range of“at least 10” inherently includes a subrange of from at least 10 to 35,a subrange of from at least 10 to 25, a subrange from 25 to 35, and soon, and each subrange may be relied upon individually and/orcollectively and provides adequate support for specific embodimentswithin the scope of the appended claims. Finally, an individual numberwithin a disclosed range may be relied upon and provides adequatesupport for specific embodiments within the scope of the appendedclaims. For example, a range “of from 1 to 9” includes variousindividual integers, such as 3, as well as individual numbers includinga decimal point (or fraction), such as 4.1, which may be relied upon andprovide adequate support for specific embodiments within the scope ofthe appended claims.

The invention has been described in an illustrative manner and it is tobe understood that the terminology which has been used is intended to bein the nature of words of description rather than of limitation. Manymodifications and variations of the present invention are possible inlight of the above teachings and the invention may be practicedotherwise than as specifically described.

1. A lubricant composition comprising: a base oil; an additive package comprising: an epoxide compound having two or more oxirane rings, wherein at least one of said oxirane rings is terminal; and an antiwear additive comprising phosphorous, wherein said additive package is present in an amount of at least 5 wt. % based on a total weight of said lubricant composition.
 2. The lubricant composition of claim 1 wherein said epoxide compound is monomeric.
 3. The lubricant composition of claim 1 wherein said epoxide compound has the general formula (VII):

wherein each Z and R¹¹ is independently a substituted or unsubstituted divalent hydrocarbon group.
 4. The lubricant composition of claim 1 wherein said epoxide compound has the formula:


5. The lubricant composition of claim 1 wherein said epoxide compound includes fewer than five oxirane rings per molecule of said epoxide compound.
 6. The lubricant composition of claim 1 wherein said epoxide compound is included in an amount of from 0.1 to 5 wt. % based on a total weight of said lubricant composition.
 7. The lubricant composition of claim 1 wherein said epoxide compound has a weight average molecular weight of from 30 to
 1500. 8. The lubricant composition of claim 1 wherein said epoxide compound has an epoxide equivalent weight of from 75 to 250 g per mole of oxirane ring in said epoxide compound.
 9. The lubricant composition of claim 1 wherein said epoxide compound has a boiling point of at least 50° C. at 1 atmosphere of pressure.
 10. The lubricant composition of claim 1 wherein said epoxide compound has a flash point of at least 25° C. at 1 atmosphere of pressure.
 11. The lubricant composition of claim 1 wherein at least 50 wt. % of said epoxide compound remains unreacted in said lubricant composition based on a total weight of said epoxide compound utilized to form said lubricant composition prior to any reaction in said lubricant composition.
 12. The lubricant composition of claim 1 wherein said lubricant composition is a crankcase lubricant composition.
 13. The lubricant composition of claim 1 wherein said base oil is included in said lubricant composition in an amount greater than 50 wt. % based on a total weight of said lubricant composition.
 14. The lubricant composition of claim 13 wherein said base oil has a viscosity of from 1 to 20 cSt when tested at 100° C. according to ASTM D445 and is selected from the group consisting of API group I oils, API group II oils, API group III oils, API group IV oils, API group V oils, and combinations thereof.
 15. The lubricant composition of claim 1 wherein said antiwear additive comprising phosphorous is a dihydrocarbyldithiophosphate salt having the general formula (XIX): [R²¹O(R²²O)PS(S)]₂M  (XIX), wherein R²¹ and R²² are each independently hydrocarbyl groups having from 1 to 20 carbon atoms, and wherein M is a metal atom or an ammonium group.
 16. The lubricant composition of claim 15 wherein said dihydrocarbyldithiophosphate salt comprises a zinc dihydrocarbyldithiophosphate salt.
 17. The lubricant composition of claim 1 wherein said antiwear additive comprising phosphorous is included in said lubricant composition in an amount of from 0.1 to 5 wt. % based on a total weight of said lubricant composition.
 18. The lubricant composition of claim 1 wherein said additive package further comprises an amine compound having a total base number of at least 80 mg KOH/g when tested according to ASTM D4739.
 19. The lubricant composition of claim 18 wherein said amine compound selected from the group consisting of: a) a sterically hindered amine compound having the general formula (XIV) or (XV):

wherein each R¹⁶ is independently a hydrogen atom or a hydrocarbyl group having from 1 to 17 carbon atoms, wherein at least two groups designated by R¹⁶ are each an alkyl group, wherein each R¹⁷ is independently a hydrogen atom or a hydrocarbyl group having from 1 to 17 carbon atoms, wherein each R¹⁸ is independently a hydrogen atom or a hydrocarbyl group having from 1 to 17 carbon atoms, wherein at least two groups designated by R¹⁸ are each an alkyl group, wherein each R¹⁹ is independently a hydrogen atom or a hydrocarbyl group having from 1 to 17 carbon atoms, and wherein the hydrocarbyl groups designated by R¹⁶, R¹⁷, R¹⁸, and R¹⁹ are each independently and optionally substituted with an alcohol group, an amide group, an ether group, or an ester group; b) a monomeric aliphatic acyclic amine compound having a molecular weight of less than 500 and consisting of covalent bonds; c) a monomeric aliphatic cyclic amine compound having a molecular weight of less than 500 and including no more than two nitrogen atoms; and d) combinations thereof.
 20. The lubricant composition of claim 18 wherein said amine compound is included in said lubricant composition in an amount of from 0.1 to 10 wt. % based on a total weight of said lubricant composition.
 21. The lubricant composition of claim 18 wherein said amine compound is a sterically hindered amine compound.
 22. The lubricant composition of claim 21 wherein said sterically hindered amine compound is (2,2,6,6-tetramethyl-4-piperidyl)dodecanoate.
 23. The lubricant composition of claim 1 wherein said additive package further comprises a dispersant.
 24. The lubricant composition of claim 23 wherein said dispersant is included in said lubricant composition in an amount of from 0.01 to 15 wt. % based on a total weight of said lubricant composition.
 25. The lubricant composition of claim 1 wherein said lubricant composition has a fluoropolymer seal compatibility such that a fluoropolymer seal submerged in said lubricant composition exhibits a change in tensile strength of from −50 to 10% when tested according to CEC L-39-T96.
 26. The lubricant composition of claim 1 wherein said lubricant composition has a fluoropolymer seal compatibility such that a fluoropolymer seal submerged in said lubricant composition exhibits a change in elongation at rupture of from −60 to 10% when tested according to CEC L-39-T96.
 27. The lubricant composition of claim 1 wherein said lubricant composition includes less than 0.5 wt. % of an epoxidized fatty acid based on a total weight of said lubricant composition.
 28. The lubricant composition of claim 1 wherein said lubricant composition has a total base number of at least 3 mg KOH/g when tested according to ASTM D2896.
 29. A lubricant composition comprising: a base oil; and an additive package comprising: an epoxide compound having two or more oxirane rings and having an epoxide equivalent weight of from 75 to 250 g per mole of oxirane ring in said epoxide compound, and an antiwear additive comprising phosphorous; wherein said additive package is present in an amount of at least 5 wt. % based on a total weight of said lubricant composition.
 30. A lubricant composition comprising: a base oil; an epoxide compound having two or more oxirane rings, wherein at least one of said oxirane rings is terminal; and an antiwear additive comprising phosphorous; wherein said lubricant composition has a total additive treat rate of at least 5 wt. % based on a total weight of said lubricant composition.
 31. A method of lubricating a system comprising a fluoropolymer seal, said method comprising: providing a lubricant composition comprising a base oil and an additive package comprising an epoxide compound including two or more oxirane rings, wherein at least one of the oxirane rings is terminal, and an antiwear additive comprising phosphorous; and contacting the fluoropolymer seal with the lubricant composition; wherein the additive package is present in an amount of at least 5 wt. % based on a total weight of the lubricant composition.
 32. An additive package for a lubricant composition, said additive package comprising: an epoxide compound having two or more oxirane rings, wherein at least one of said oxirane rings is terminal; and an antiwear additive comprising phosphorous.
 33. The additive package of claim 32 wherein said additive package consists essentially of said epoxide compound and said antiwear additive comprising phosphorous. 